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 0.5M 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 2M hydrochloric acid (20 ml). The aqueous solution was washed with diethyl ether, basified with 5M sodium hydroxide and extracted with ethyl acetate.

Provenance & Evidence