Sodium Sulfate → {4-[2-(Dimethylamino)ethoxy]phenyl}methanol

Participants

Reaction Steps

Methyl 4-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoate (for a preparation see Intermediate 19) (1.61 g, 6.79 mmol) in THF (40 mL) was cooled in ice and then treated with a 1M solution of LiAlH4 in diethyl ether (6.8 ml) and the mixture was stirred under nitrogen for 4 h. The reaction mixture was cautiously treated with saturated aq. sodium sulfate solution until the hydrogen evolution ceased. The mixture was then stirred under nitrogen for 1 h and filtered. The solid was washed with diethyl ether and the combined filtrate and washings evaporated under reduced pressure to give the title compound (1.32 g, 100%). LCMS (System B) RT=1.70 min, ES+ve m/z 196 (M+H)+.

Provenance & Evidence