Hydrochloric Acid → Ethyl 2-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)propanoate

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Reaction Steps

Under a nitrogen atmosphere, 60% sodium hydride (1.13 g) was added to a solution in N,N-dimethylformamide (65 ml) of ethyl 3,4-ethylenedioxyphenylacetate [M. Sasamoto, Chem. Pharm. Bull., 8, 324 (1969)] (6.00 g) in an ice bath. Thereafter, methyl iodide (1.76 ml) was added dropwise and the resulting mixture was stirred under ice-cooling for 4 hours. To the reaction mixture was added 1 N hydrochloric acid and the resulting mixture was subjected to extraction with diethyl ether, after which the extraction solution was washed with water and then dried. The solvent was removed by distillation under reduced pressure and the residue was purified by a silica gel column chromatography to obtain the desired compound (5.57 g).

Provenance & Evidence