Benzyl 3-hydroxybutanoate → Benzyl crotonate, (E)-

Participants

Reaction Conditions

Reaction Steps

Benzyl 3-hydroxyl-butanoate (Sakaki et al., Chem. Pharm. Bull., 37, p. 2952 (1989)) (0.46 g, 2.4 mmol), CuCl (11 mg, 5 mol %), and 1 (0.7 g, 110 mol %) were combined in 20 mL of dry CH3CN and heated to 60° C. for 16 h. The reaction mixture was cooled and evaporated, followed by isolation according to the general procedure to give benzyl crotonate (0.346 g, 83%) as a mobile oil: IR 3060, 3030, 1720; 1H NMR δ 7.40-7.20 (m, 5H), 7.00 (dq, 1H, J=15.5, 6.9), 5.86 (dq, 1H, J=16.0, 1.6), 5.18 (s, 2H), 1.83 (dd, 3H, J=1.7, 6.9).

Provenance & Evidence