4442-54-0, 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
The synthesis of ecfo-8-methyl-8-azabicyclo[3.2.1 ]oct-3-yl 2,3-dihydro- l ,4- benzodioxine-6-carboxylate (Compound 7) is illustrated in Synthesis Scheme 2 (Figure 3). A solution of 1 ,4-benzodioxane-6-carboxylic acid, 1 (3.5 g, 1 9.43 mmol) in dichloromethane (35 mL) at room temperature under argon atmosphere was treated with thionyl chloride (35 mL, 479.83 mmol) and stirred for 3 h under reflux. The solution was then concentrated to leave the acid chloride as a dark black solid. The solid was then coevaporated with dichloromethane (2×25 mL) and dried under vacuum to remove the volatile impurities. The dark black solid was then dissolved in dry THF (35 mL). Meanwhile, on a separate flask, a solution of tropine, 2 (2.9 g, 20.54 mmol) in dry THF (30 mL) at 5 ¡ãC under argon atmosphere was treated with n-butyl lithium (0.5 M in hexanes, 20.6 mL, 1 0.27 mmol) and stirred for 30 min. at the same temperature. A solution of the acid chloride was added to the alkoxide solution at 5¡ãC dropwise. After completion of addition, the reaction mixture was allowed to warm to room temperature and stirred for another 16 h at the same temperature. The reaction was monitored with TLC. After completion, the reaction mixture was evaporated under vacuum. The residue was dissolved in dichloromethane ( 100 mL), washed with water (3 x50 mL), saturated brine (50 mL), dried over Na2S04. The organic layer was filtered and evaporated under vacuum. The crude product was purified by flash column chromatography (neutral alumina) using a mixture of 80percent EtOAc in pet ether as eluent to provide the product (2.3 g) as a pale yellow solid. The compound was further purified by recrystallisation using diethyl ether and n-hexanes to afford Cpd-7 ( 1 .2 g, 20.36percent) as a colorless solid. R/: 0.3 (30percent MeOH in CHC13). 1H-NMR (DMSO-tft): delta 1 .63(s, 1 H), 1 .68 (s, 1 H), 1 .87-2.09 (m, 6H), 2.1 7 (s, 3H), 3.03 (s, 2H), 4.28-4.33 (m, 4H), 5.04-5.07 (m, 1 H), 7.00 (d, J=8.4Hz, 1 H), 7.38 (d, J= 1 .8Hz, 1 H), 7.45 (dd, J=8.4Hz, 1 .8Hz, 1 H). LC-MS m/z: 304 [M + H]+
4442-54-0, 4442-54-0 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid 2758833, abenzodioxans compound, is more and more widely used in various fields.
Reference£º
Patent; BUCK INSTITUTE FOR RESEARCH ON AGING; JOHN, Varghese; BREDESEN, Dale E.; WO2013/19901; (2013); A2;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem