Hydrochloric Acid → HCID 54407823, compound

Participants

Reaction Steps

30 ml of methanol and 20 ml of dichloromethane were added to 7.4 g (25.6 mmol) of 5-chloro-6-ethoxycarbonyl-8-fluorothiochroman-4-one (corresponding to compound of the formula (VIII)). While the mixture was maintained at a temperature not exceeding 0° C. with a sodium chloride aqueous solution and an ice bath, 0.97 g (25.6 mmol) of sodium borohydride as a reducing agent was gradually added. The mixture was allowed to react at room temperature for 3 hours, and then the reaction mixture was poured into a 5% hydrochloric acid aqueous solution and extracted with dichloromethane. The resultant organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel; hexane:ethyl acetate=2:1) to give 2.9 g (yield 40%) of 4-hydroxy-5-chloro-6-ethoxycarbonyl-8-flurothiochroman (corresponding to compound of the formula (IX)).

Provenance & Evidence