Ammonia → Methyl 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propionate

Participants

Reaction Steps

4.2 g of methyl 3-[5-(3-methoxycarbonylpropionyloxy)-4,6,7-trimethyl-1,3-benzoxathiole-2-yl]propionate (prepared as described in Example 31) were added to a mixture of 50 ml of methanol and 14 g of 28% w/v aqueous ammonia, and the mixture was reacted for 20 hours at room temperature. The volatile matter was then evaporated from the reaction mixture under reduced pressure, and ethyl acetate was added to the residue. The ethyl acetate solution was washed with water and dried over anhydrous sodium sulfate. The ethyl acetate was then distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the desired compound was obtained from the fraction eluted with a 20:1 by volume mixture of benzene and ethyl acetate.

Provenance & Evidence