Benzenesulfonyl chloride → HCID 10680344, compound

Participants

Reaction Steps

A solution of (-)-(2S,3S)-3-hydroxy-2-methyl-7-phenylheptanoic acid (0.79 g, 3.3 mmol) in pyridine (30 mL) is cooled to 0° C. and benzenesulfonyl chloride (0.85 mL, 6.7 mmol) is added over 1 minute. The reaction is stirred in ice for 5 minutes, at room temperature for 2 hours and then at 0° C. for 16 hours. The reaction is poured into ice (40 mL) and extracted with ether (100 mL). The organic phase is washed with NaHCO3 (30 mL), 1N HCl (2×20 mL) and water (2×30 mL). The organic phase is dried over MgSO4 and concentrated in vacuo. The crude product is purified by column chromatography (silica, 25% ether in petroleum ether) to give (3S,4S)-3-Methyl-4-(4-phenylbutyl)oxetan-2-one (0.28 g, 39%): 1H NMR (300 MHz, CDCl3) δ 7.31-7.21 (m, 2H), 7.19-7.15 (m, 3H), 4.19-4.13 (m, 1H), 3.25-3.16 (m, 1H), 2.64 (t, J=7.6 Hz, 2H), 1.95-1.64 (m, 4H), 1.55-1.40 (m, 2H), 1.36 (d, J=7.8 Hz, 3H); MS (EI) m/e 218 (M+).

Provenance & Evidence