Tropic acid → 3-Phenyloxetan-2-one

Participants

Reaction Conditions

Reaction Steps

Diethylazodicarboxylate (DEAD) (1.89 milliliter (mL), 12.0 millimole (mmol)) was added dropwise to a stirred solution of triphenylphosphine (3.18 gram (g), 12.0 mmol) in dry tetrahydrofuran (THF) (40 mL) at −78° C. under nitrogen (N2). Tropic acid (2.00 g, 12.0 mmol) in dry THF (40 mL) was then added dropwise, and the resulting mixture was stirred and slowly warmed to −10° C., at which point the solution was homogeneous. After concentration and purification by flash chromatography on silica gel (petroleum ether/ethyl acetate (EtOAc) 85:15), 3-phenyloxetan-2-one (1.49 g, 84%) (see Mulzer, J.; Kerkmann, T. J. Am. Chem. Soc. 1980, 102, 3620-3622) was isolated as a yellow oil: 1H NMR (270 MHz, CDCl3) δ 7.3 (m, 5H), 4.8 (dd, J=5.0, 1.7 Hz, 1H), 4.5 (dd, J=5.0, 1.7 Hz, 1H), 4.2 (dd, J=5.0, 5.0 Hz, 1H).

Provenance & Evidence