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

Participants

Reaction Steps

A 2.5 M solution of lithium aluminum hydride in THF (10 mL) was slowly added to a solution of methyl ester 1b (7.30 g, 0.04 mol,) in 100 mL of anhydrous THF. After completion of the addition, the solution was refluxed for four hours, then cooled to room temperature. Hydrochloric acid (10%, 25 mL) was then slowly added, and the resulting mixture was heated for another 30 minutes. After cooling to room temperature, diethyl ether (100 mL) was added, the organic layer was separated and washed with brine, dried with anhydrous magnesium sulfate. Evaporation of the solvent gave the alcohol 1c (5.4 g, 90%) as a colorless oil. 1H NMR (250 MHz, 25° C., CDCl3): δ 7.12 (m, 1H, Ar—H), 6.92 (m, 1H, Ar—H), 6.79 (m, 1H, Ar—H), 3.62 (t, 2H, CH2OH), 2.86 (t, 2H, Ar—CH2), 2.30 (s, 1H, OH), 2.00 (m, 4H, CH2CH2CH2CH2).

Provenance & Evidence