Sodium Hydroxide → 3-Amino-1-(thiophen-3-yl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of LAH (1.45 g, 38.1 mmol) in dry THF (120 mL) was added a solution of 3-oxo-3-(thiophen-3-yl)propanenitrile (4.8 g, 31.8 mmol) in dry THF (40 mL) dropwise at 0° C. under nitrogen atmosphere. The mixture was warmed to 25° C. and then heated at 65° C. for 6 hours. After cooling to 0° C., a saturated solution of sodium hydroxide (2 mL) was added dropwise and the mixture was filtered. The filtrate was concentrated to dryness to give crude 3-amino-1-thiophen-3-yl-propan-1-ol which was used in next step without further purification. 1H NMR (300 MHz, CDCl3): δ 7.29-7.26 (m, 2H), 7.05 (dd, 1H, J1=4.8 Hz, J2=1.2 Hz), 5.04 (dd, 1H, J1=8.1 Hz, J2=3.0 Hz), 3.10-3.05 (m, 2H), 1.82-1.77 (m, 2H).

Provenance & Evidence