Ethanol → HCID 86757173, compound

Participants

Reaction Steps

Sodium borohydride (NaBH4) (0.36 g, 9.7 mmol) is added at 0° C. to a solution of the previous 6-formyl-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran (2.00 g, 9.7 mmol) in 20 ml of ethanol. The agitation was continued at this temperature for 30 minutes. After evaporation of the ethanol, it is taken up again in 100 ml of ethyl ether and acidified by an aqueous 3N solution of HCl to pH 1. The mixture is extracted with ether, dried over MgSO4 filtered and the solvents evaporated. The crude product is purified by flash chromatography on silica (eluent petroleum ether:ethyl ether:100:10). 1.85 g of 6-(hydroxymethyl-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyrane is obtained (gross yield=92%).

Provenance & Evidence