m-Chloroperbenzoic acid → HCID 12716095, compound

Participants

Reaction Steps

To a solution of allylic alcohol 7 (5.0 g, 33.7 mmol) in dry CH2Cl2 (60 mL) at 0° C. was added m-chloroperbenzoic acid (8.7 g, 50.6 mmol) in small portions. The resulting solution was stirred for 8 h until complete consumption of starting materials (the progress of the reaction was monitored by TLC). The reaction mixture was quenched with water and the aqueous layer was extracted with CH2Cl2 (3×30 mL). The organic layer was washed with aq. 10% solution of NaHCO3 (15 mL). The combined organic layer was dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography over silica gel using petroleum ether/EtOAc (4:1) to give the corresponding epoxide 8 (4.8 g, 88%) as a viscous gum. IR: (CHCl3, cm−1): νmax 700, 991, 1028, 1055, 1106, 1452, 2921, 3404; 1H NMR (200 MHz, CDCl3): δ 2.88-2.99 (m, 3H), 3.17-3.23 (m, 1H), 3.57-3.72 (m, 1H), 3.85-3.95 (m, 1H), 7.18-7.34 (m, 5H); 13C NMR (50 MHz, CDCl3): δ 34.2, 67.1, 78.9, 87.5, 125.5, 127.5, 128.4, 140.8; Anal. Calcd for C10H12O2: C, 73.15; H, 7.37. Found: C, 73.25; H, 7.47%.

Provenance & Evidence