(R)-(-)-Benzyl glycidyl ether

100-39-0

60456-23-7

14618-80-5

NaH (179 mg, 4.10 mmol, 55% oil solution) was suspended in THF (2 mL) and cooled to 0 °C under argon protection. A THF solution (4 mL) of (S)-oxiran-2-ylmethanol (S1, 200 mg, 2.70 mmol) and benzyl bromide (0.340 mL, 2.86 mmol) were added sequentially. The reaction mixture was heated and stirred at reflux for 19 hours. After completion of the reaction, the reaction was quenched with 0.1 M phosphate buffer (pH 6.5). The product was extracted with ethyl acetate (3×) and the organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by fast column chromatography on silica gel (eluent: hexane/ethyl acetate = 10/1) to afford (R)-benzyloxymethylepoxane (S21) as a colorless oil (196 mg, 44%).1H NMR (300 MHz, CDCl3) δ = 2.62 (dd, J1 = 2.5 Hz, J2 = 5.0 Hz, 1H), 2.80 (dd, J1 = 3.0 Hz, J2 = 5.0 Hz, 1H), 3.19 (dd, J1 = 2.5 Hz, J2 = J3 = 3.0 Hz, J4 = 5.5 Hz, 1H), 3.44 (dd, J1 = 5.5 Hz, J2 = 11.5 Hz, 1H), 3.77 (dd, J1 = 3.0 Hz, J2 = 11.5 Hz, 1H), 4.57 (d, J = 12.0 Hz, 1H), 4.61 (d, J = 12.0 Hz, 1H), 7.25-7.38 (m, 5H); 13C NMR (75 MHz, CDCl3) δ = 44.3, 50.8, 70.8, 73.3, 127.7, 128.4, 137.8; HRMS (EI) m/z 164.0825 (calculated for C10H12O2, M+ 164.0837).