Water → 4-(Dimethylaminomethyl)-2-thiophenemethanol

Participants

Reaction Steps

A solution of 5-(hydroxymethyl)-N,N-dimethyl-3-thiophenecarboxamide (1.7 g) in dry tetrahydrofuran (150 ml) was treated with a 0.5 M solution of aluminium hydride in tetrahydrofuran (26 ml). After 2 h at room temperature, water (5 ml) was cautiously added and the mixture was filtered through diatomaceous earth. The filtrate was evaporated to leave an oily residue, which was dissolved in 2 M hydrochloric acid (20 ml). The aqueous solution was washed with diethyl ether, basified with 5 M sodium hydroxide and extracted with ethyl acetate.

Provenance & Evidence