Methyl 4-benzoylbutyrate → 1-Phenylpentane-1,5-diol

Participants

Reaction Steps

A 2.0 M tetrahydrofuran solution of lithium aluminum hydride (2.80 mL, 5.60 mmol) was added to a tetrahydrofuran solution (10 mL) of methyl 5-oxo-5-phenylpentanoate (500 mg, 2.78 mmol) at 0° C. The reaction mixture was stirred for one hour and quenched with the sequential addition of water (0.2 mL), 10% sodium hydroxide solution (0.2 mL), and water (0.6 mL). It was concentrated in vacuo to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.32-1.42 (m, 1H), 1.46-1.55 (m, 1H), 1.56-1.64 (m, 2H), 1.70-1.78 (m, 1H), 1.78-1.88 (m, 1H), 3.63 (t, J=6.6 Hz, 2H), 4.68 (dd, J=5.7, 7.8 Hz, 1H), 7.25-7.30 (m, 1H), 7.32-7.35 (m, 4H).

Provenance & Evidence