Hydrochloric Acid → 4-(Thiophen-2-yl)butan-1-ol

Participants

Reaction Steps

To a cool (0°) solution of 10.0 g of 4-thienylbutyric acid (58.8 mmol) in 60 ml of dry THF was added 59 ml of a 1M solution of borane in THF, dropwise with stirring over one hour. The mixture was stirred for an additional 5 hours. The reaction mixture was poured onto 200 g of ice. This mixture was acidified with 2N HCl and the product extracted into ethyl acetate. The extract was washed with brine, dried (Na2SO4) and evaporated to give 8.5 g of a colorless oil (93%). 1H-NMR (CDCl3)δ7.0 (1H, t); 6.75 (2H, m); 3.5 (2H, t); 2.75 (2H, t); 1.6 (4H, m).

Provenance & Evidence