Water → N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide

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Reaction Steps

To a solution of N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (1.00 g, 4.94 mmol) in methanol (20 mL) at 0° C. is added sodium borohydride (0.50 g, 7.41 mmol). The reaction is stirred for 1.5 hours, whereupon water is added and the volatiles are removed in vacuo. The mixture is extracted with dichloromethane and the organic phase is dried over sodium sulfate, filtered, and concentrated to give N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide, which is used in the next step without further purification.

Provenance & Evidence