Diethyl Ether → 2-(3,5-Dimethoxyphenylthio)benzyl alcohol

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Reaction Steps

To a stirred solution of 12.3 g of the 2-(3,5-dimethoxyphenylthio)benzoic acid, prepared in Example 1, in 50 ml of anhydrous tetrahydrofuran was added 1.8 g of sodium borohydride portionwise at 0° C. After 30 minutes, the resulting solution was treated with 6.3 ml of BF3. Et2O at the same temperature and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and dilute hydrochloric acid, and the ethyl acetate layer was successively washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (eluting solvent; hexane:ethyl acetate=3:1) to give 8.3 g (71%) of a compound of the indicated formula (11).

Provenance & Evidence