m-Chloroperbenzoic acid → HCID 131735543, compound

Participants

Reaction Steps

To a stirred solution of compound 11 (13.7 g, 36.8 mmol) in dichloromethane (300 mL), m-CPBA (15.9 g, 92.0 mmol) was added portion wise at room temperature. The mixture was stirred at room temperature for 16 h, quenched with a saturated NaHCO3 solution and extracted with DCM (200 mL×2). The combined organic layer was washed with brine (100 mL×2) and dried over Na2SO4. The solvent was removed under reduced pressure and residue was purified by silica gel column chromatography (3% EtOAc/Hexane) to give epoxide 12 (12.2 g, 85%) as an oil. [α]24D +18.25° (c 1.0, CHCl3); 1H NMR (500 MHz, CDCl3) δ 1.00-1.11 (m, 28H), 2.30 (in, 1H,), 3.05 (s, 1H), 3.37 (s, 1H), 3.56 (d, J=2.5 Hz, 1H), 3.99-4.05 (m, 2H), 4.19 (d, J=5.0 Hz, 1H), 4.26 (dd, J=3.0, 11.5 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 12.6, 13.1, 13.3, 17.0, 17.1, 17.2, 17.3, 17.4, 17.5, 48.2, 55.5, 58.4, 64.7, 70.7, 75.0; HR-MS Calcd. For (C18H36O5Si2+H)+ 389.2101. found 389.2171.

Provenance & Evidence