Benzenesulfonyl chloride → HCID 18790043, compound

Participants

Reaction Conditions

Reaction Steps

To a solution containing (-)-2-(2-benzenesulfonylethyl)-3-hydroxy-7-phenylheptanoic acid (1 g, 2.56 mmol) in anhydrous pyridine (17 mL) under nitrogen atmosphere at 0° C. is added freshly distilled benzenesulfonyl chloride (0.89 g, 5.13 mmol) via syringe. The resulting dark yellow/orange-colored solution is cooled to -20° C. After 16 hours, the mixture is partitioned between ice/water (100 mL) and ethyl acetate (50 mL) and the layers are separated. The aqueous phase is extracted with ethyl acetate (2×50 mL) and the combined organic extracts are washed successively with water (4×50 mL), brine (50 mL), dried over anhydrous MgSO4, filtered and concentrated to afford a yellow oil. The crude product is combined with the product of an identical reaction performed on 1.55 g-scale and chromatographed on silica gel (pet-ether/EtOAc, 4:1) to afford (-)-3-(2-benzenesulfonyl-ethyl)-4-(4-phenylbutyl)-oxetan-2-one (1.07 g, 44%) as a pale yellow oil. TLC analysis [pet-ether/EtOAc, 2:1, Rf (acid)=0.05, Rf (lactone)=0.65]. [α]23D -10.1° (c 1.0, CHCl3); 1H NMR (300 MHz, CDCl3) δ 1.36-1.80 (m, 6H), 2.16 (m, 2H), 2.62 (t, J=7.5 Hz, 2H), 3.16 (m, 1H), 3.35 (m, 1H), 3.79 (m, 1H), 4.56 (m, 1H), 7.16 (m, 3H), 7.28 (m, 2H), 7.69 (m, 2H), 7.79 (m, 1H), 7.91 (m, 2H) ppm. Mass spectrum (EI) m/z 373 (M+H)+.

Provenance & Evidence