Hydrochloric Acid → (E)-3-(4'-chloro-biphenyl-4-yl)-but-2-en-1-ol

Participants

Reaction Steps

A 1M solution of DIBAL-H in toluene (10 ml, 10 mmol) was added dropwise, at −70° C. over 10 min, to a stirred solution of (E)-ethyl-3-(4′-chloro-biphenyl-4-yl)-but-2-enoate (1.0 g, 3.32 mmol) in dry THF (25 ml), and the mixture warmed to room temperature over 4 h. Methanol (1 ml) was carefully added, followed by 1N HCl (50 ml) and the resulting mixture extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give the product, (E)-3-(4′-chloro-biphenyl-4-yl)-but-2-en-1-ol as a colourless solid: 0.86 g (100%).

Provenance & Evidence