Cyclopentanone → 4-(1-Hydroxycyclopentyl)benzonitrile

Participants

Reaction Steps

According to Example 2, the Grignard reagent 1C (freshly prepared via bromine-magnesium exchange[6] from 4-bromo-benzonitrile (400 mg, 2.20 mmol, 1.10 equiv) and i-PrMgCl.LiCl (1.00 M in THF; 2.16 mL, 2.16 mmol, 1.08 equiv) at −20° C.) was reacted with cyclopentanone (168 mg; 2.00 mmol) in the presence of LaCl3.2LiCl (0.33 M; 6.06 mL, 2.00 mmol, 1.00 equiv). The crude product was purified by flash column chromatography (silica; pentane:Et2O, 7:3) to give the desired product as a colorless oil (355 mg, 95%).

Provenance & Evidence