Water → 5,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

Participants

Reaction Steps

A solution of 6,7-dihydro-5H-benzo[b]thiophen-4-one oxime (1.67 g) in dry dichloromethane (100 mL) was cooled to 0°. Following dropwise addition of diisobutylaluminum hydride (50 ml, 1M in hexanes), the mixture was stirred at 0° for three hours and then diluted with dichloromethane (50 mL). Sodium fluoride (8.4 g) was added, followed by water (2.7 mL). The reaction mixture was stirred vigorously for 30 minutes, then filtered and concentrated to provide the title compound (0.81 g) as a white solid.

Provenance & Evidence