Category: 274910-19-9

(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, cas is 274910-19-9, it is a common heterocyclic compound, the benzodioxans compound, its synthesis route is as follows.,274910-19-9

A solution of 20 (3.75 g, 32.3 mmol) in diethyl ether (80 mL) was cooled to 0 C and phosphorous tribromide (3.67 mL, 38.8 mmol) was added dropwise. The solution was stirred at 0 C for 10 min, then at r.t. for 1 h. Water (10 mL) was added cautiously to quench the excess of reagent and the mixture was diluted with diethyl ether and washed with water (3 x 50 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure to obtain 21 as a brown solid (4.61 g, 62%). 1H NMR (CDCI3) delta 6.91-6.77 (m, 3H), 4.52 (s, 2H), 4.35-4.33 (m, 2H), 4.29-4.27 (m, 2H). Found: [M+H- Br]=149.5.

274910-19-9 is used more and more widely, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol

Reference£º
Patent; THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.; UPTON, Anna, Marie; COOPER, Christopher, Blair; MARCEL, Koenraad, Jozel Lodewijk; GUILLEMONT, Jerome, Emile Goerges; VAN DEN BROECK, Walter Marcel, Mathilde; PALMER, Brian, Desmond; MA, Zhenkun; (186 pag.)WO2017/155909; (2017); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to benzodioxans compound, name is (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, and cas is 274910-19-9, its synthesis route is as follows.,274910-19-9

A solution of 2,3-dihydro-1,4-benzodioxin-5-ylmethanol (Intermediate A1) (commercially available from Aldrich) (3 g, 18.1 mmol) in THF (100 mL) was treated with manganese(IV) oxide, activated (commercially available from Aldrich): MnO2 (10 g, 115 mmol) at rt. The mixture was heated to 35 C. for 2 h and 60 C. for 4 h followed by 18 h at room temperature (rt). The mixture was filtered through celite and the solvent was removed under vacuum. The residue was purified by chromatography on silica gel with 20% EtOAc:hexanes to give 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde (Intermediate A2) 2.6 g (88%). A mixture of 4-iodo-1-tritylimidazole (commercially available) (8.64 g, 19.8 mmol) in dichloromethane (100 mL) at -10 C. was treated with ethyl magnesium bromide (6.3 mL, 19 mmol, 3M in THF) and allowed to react for 45 m. A solution of 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde (Intermediate A2) (2.6 g, 15.9 mmol) in dichloromethane was added via syringe at -10 C. and stirred for 45 m. The mixture was quenched with water (50 mL) and a sat. solution of ammonium chloride (50 mL). The residue was isolated in a typical aqueous workup and purified by chromatography on silica gel with 3 to 5% NH3-MeOH:CH2Cl2 to give (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (Intermediate A3) as a solid, 2.9 g (40%). A solution of (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (Intermediate A3) (1 g, 2.11 mmol) in dichloromethane (30 mL) was reacted with TFA:trifluoroacetic acid (5.3 mL, 68 mmol)) and triethylsilane (TES) (2.8 mL, 17 mmol) at rt for 24 h. The mixture was evaporated under reduced pressure and quenched with solid NaHCO3. This material was subjected to an aqueous work-up and the residue was purified by chromatography on silica gel with 5% NH3-MeOH:CH2Cl2 to yield 5-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1H-imidazole (Intermediate A4) 330 mg (72%). A mixture of 5-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1H-imidazole (Intermediate A4) (260 mg, 1.2 mmol) in THF (10 mL) and water (10 mL) was treated with NaHCO3 (1 g, 12 mmol) and phenylchlorothionoformate (0.42 mL, 3.13 mmol) for 3 h at rt. The mixture was diluted with diethyl ether (35 mL) and water (10 mL). The aqueous layer was removed and extracted with ether (2¡Á10 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated under vacuum. The residue was treated with triethylamine (1 mL) in methanol (9 mL) at rt for 16 h. The solvent was removed and the product was isolated and purified either by tituration with CH2Cl2:hexane or by chromatography on SiO2 with EtOAc or 3% MeOH:CH2Cl2. This gave 4-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound-1) 150 mg (50%). 1H NMR (300 MHz, DMSO-d6 w/TMS): delta 11.9 (brs, 1H), 11.7 (s, 1H), 6.76-6.65 (m, 3H), 6.41 (s, 1H), 4.28-4.21 (m, 4H), 3.61 (s, 2H).

With the complex challenges of chemical substances, we look forward to future research findings about 274910-19-9,belong benzodioxans compound

Reference£º
Patent; Allergan, Inc.; US2006/69144; (2006); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO205,mainly used in chemical industry, its synthesis route is as follows.,274910-19-9

2,3-Dihydro-1,4-benzodioxin-5-ylinethanol (1.01 g, 6.07 mmol) was dissolved in methylene chloride (60 mL). Manganese dioxide (3.81 g, 43.8 mmol) was added, and then the mixture was stirred in a nitrogen atmosphere at room temperature for 24 hours. Manganese dioxide was separated by filtration and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane = 1/4) to give the target compound (835 mg, yield: 84%) as a colorless oil. 1H-NMR (CDCl3, 400MHz):delta ppm: 4.32-4.34 (2H, m), 4.38-4.41 (2H, m), 6.91 (1H, t, J=7.8Hz), 7.10 (1H, dd, J=1.6, 7.8Hz), 7.40 (1H, dd, J=1.6, 7.8Hz). MS (EI) m/z: 164.0468 (M+)

With the complex challenges of chemical substances, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,belong benzodioxans compound

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP1914229; (2008); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belong benzodioxans compound,(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,274910-19-9,Molecular formula: C9H10O3,mainly used in chemical industry, its synthesis route is as follows.,274910-19-9

N5-Cyclobutyl-N3-methyl-2-oxo-1, 2-d ihydropyrid ine-3,5-d icarboxamide (50 mg, 0.201mmol), (2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methanol (50.0 mg, 0.301 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.166 mL, 0.632 mmol) were combined in toluene (1.5 mL)and the reaction mixture heated in a 5 mL microwave vial on a Biotage Initiator microwave at 120C for 30 mm. The reaction mixture was poured onto water (20 mL), and extracted with ethylacetate (3 x 10 mL). The combined organic portions were evaporated in vacuo to yield the crude product as a brown oil. The product was loaded in dichloromethane onto a 25 g SNAP silica cartridge and purified via Biotage 5P4 flash chromatography, eluting from 50 – 100 % ethyl acetate/cyclohexane. The relevant fractions were combined and evaporated in vacuo – yielding 76mg of product. The sample was dissolved in MeOH/DMSO (1 mL, 1:1) and purified by MDAP (Formic). The solvent was evaporated in vacuoto give the required product – N5-cyclobutyl-1-((2,3- dihyd robenzo[b] [1,4]d ioxin-5-yl)methyl)-N3-methyl-2-oxo-1, 2-d ihydropyrid ine-3,5-dicarboxamide(40 mg, 0.096 mmol, 47.7 % yield).LCMS (2 mm Formic): Rt = 0.95 mi [MH] = 398.1.

With the synthetic route has been constantly updated, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,belong benzodioxans compound

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, cas is 274910-19-9, it is a common heterocyclic compound, the benzodioxans compound, its synthesis route is as follows.

274910-19-9, [00209j A mixture of Intermediate 1(500mg, 1.5 mmol), (2,3-dihydrobenzo[b][1,4] dioxin-5-yl)methanol (380 mg, 2.3 mmol) and Cs2CO3 (1000 mg, 3.1 mmol) in DMSO (5 mL) was stirred for 2 days at 120 C. The reaction mixture was diluted with water andbrine (1:1, 50 mL) and extracted with EtOAc (2 x 30 mL). The combined organics were washed with brine, dried over Na2504 and concentrated in vacuo. The crude product was purified by column chromatography to yield the Example 2A (400 mg, 0.97 mmol, 63% yield), as a brown oil. MS (ESI) m/z 412.2 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WURTZ, Nicholas R.; VIET, Andrew Quoc; SHAW, Scott A.; VOKITS, Benjamin P.; KICK, Ellen K.; VALENTE, Meriah Neissel; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; JUSUF, Sutjano; (140 pag.)WO2016/40417; (2016); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO279,mainly used in chemical industry, its synthesis route is as follows.,274910-19-9

(2, 3-Dihydrobenzor1, 41dioxin-5-yl)-chloromethane; Dissolve (2,3-Dihydrobenzo [1, 4] dioxin-5-yl) methanol (1.8 g, 10.8 mmol) in dichloromethane (15 mL). Add neat thionyl chloride (2 mL, 27.4 mmol) dropwise to the stirring reaction mixture at 25C under nitrogen. Stir the reaction for 15 minutes and concentrate under reduced pressure to obtain 2.0 g (100%) of the desired compound as a yellow oil. HRMS : m/z = 184.0290 (M)

With the synthetic route has been constantly updated, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,belong benzodioxans compound

Reference£º
Patent; ELI LILLY AND COMPANY; WO2003/76442; (2003); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to benzodioxans compound, name is (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, and cas is 274910-19-9, its synthesis route is as follows.,274910-19-9

A solution of the above alcohol (3.75 g, 32.3 mmol) in Et2O (80mL) was cooled to 0 C and phosphorous tribromide (3.67 mL, 38.8mmol) was added dropwise. The solution was stirred at 0 C for 10min, then at 20 C for 1 h. Water (10 mL) was added cautiously toquench the excess of reagent and the mixture was diluted withdiethyl ether and washed with water (3 50 mL). The combinedorganic layers were washed with brine (100 mL), dried over Na2-SO4, filtered and concentrated under reduced pressure to obtain5-(bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine as a brownsolid (4.61 g, 62%). 1H NMR (CDCl3, 400 MHz) d 6.91-6.77 (m,3H), 4.52 (s, 2H), 4.35-4.33 (m, 2H), 4.29-4.27 (m, 2H). Found:[M+H-Br] = 149.5.

With the complex challenges of chemical substances, we look forward to future research findings about 274910-19-9,belong benzodioxans compound

Reference£º
Article; Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D.; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1797 – 1809;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO323,mainly used in chemical industry, its synthesis route is as follows.,274910-19-9

(3) 2,3-ethylenedioxybenzyl chloride 4.3 g of 2,3-ethylenedioxybenzyl alcohol was dissolved in 50 ml of dry dichloromethane. Then, 2.1 ml of dry pyridine was dropwise added thereto, and 3.8 ml of thionyl chloride was gradually added under cooling. The reaction solution was returned to room temperature and then the reaction solution was refluxed for 3 hours on a hot water bath at 60 C. The reaction solution was concentrated under reduced pressure to obtain a syrup, which was then dissolved in 300 ml of ethyl acetate. The solution was washed with 200 ml of 0.1N hydrochloric acid and then twice with 200 ml of a saturated sodium chloride aqueous solution. Then, the solution was dried over anhydrous magnesium sulfate. The inorganic salt was removed by filtration, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (n-hexane/ethyl acetate=60/1) to obtain 4.0 g of the above identified compound as syrup. Rf: 0.64 (n-hexane/ethyl acetate=2/1).

With the synthetic route has been constantly updated, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol,belong benzodioxans compound

Reference£º
Patent; Banyu Pharmaceutical Co., Ltd.; US5122523; (1992); A;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to benzodioxans compound, name is (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, and cas is 274910-19-9, its synthesis route is as follows.

N5-Cyclobutyl-N3-methyl-2-oxo-1, 2-d ihydropyrid ine-3,5-d icarboxamide (50 mg, 0.201mmol), (2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methanol (50.0 mg, 0.301 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.166 mL, 0.632 mmol) were combined in toluene (1.5 mL)and the reaction mixture heated in a 5 mL microwave vial on a Biotage Initiator microwave at 120C for 30 mm. The reaction mixture was poured onto water (20 mL), and extracted with ethylacetate (3 x 10 mL). The combined organic portions were evaporated in vacuo to yield the crude product as a brown oil. The product was loaded in dichloromethane onto a 25 g SNAP silica cartridge and purified via Biotage 5P4 flash chromatography, eluting from 50 – 100 % ethyl acetate/cyclohexane. The relevant fractions were combined and evaporated in vacuo – yielding 76mg of product. The sample was dissolved in MeOH/DMSO (1 mL, 1:1) and purified by MDAP (Formic). The solvent was evaporated in vacuoto give the required product – N5-cyclobutyl-1-((2,3- dihyd robenzo[b] [1,4]d ioxin-5-yl)methyl)-N3-methyl-2-oxo-1, 2-d ihydropyrid ine-3,5-dicarboxamide(40 mg, 0.096 mmol, 47.7 % yield).LCMS (2 mm Formic): Rt = 0.95 mi [MH] = 398.1.

274910-19-9, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,274910-19-9 ,(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

274910-19-9, (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,274910-19-9

A solution of the above alcohol (3.75 g, 32.3 mmol) in Et2O (80mL) was cooled to 0 C and phosphorous tribromide (3.67 mL, 38.8mmol) was added dropwise. The solution was stirred at 0 C for 10min, then at 20 C for 1 h. Water (10 mL) was added cautiously toquench the excess of reagent and the mixture was diluted withdiethyl ether and washed with water (3 50 mL). The combinedorganic layers were washed with brine (100 mL), dried over Na2-SO4, filtered and concentrated under reduced pressure to obtain5-(bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine as a brownsolid (4.61 g, 62%). 1H NMR (CDCl3, 400 MHz) d 6.91-6.77 (m,3H), 4.52 (s, 2H), 4.35-4.33 (m, 2H), 4.29-4.27 (m, 2H). Found:[M+H-Br] = 149.5.

As the paragraph descriping shows that 274910-19-9 is playing an increasingly important role.

Reference£º
Article; Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D.; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1797 – 1809;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem