Sodium Sulfite → HCID 66336272, compound

Participants

Reaction Steps

3-Chloroperbenzoic acid (1.43 g of 50%, 4.14 mmol) was added to an ice-cooled mixture of 94 (500 mg, 1.97 mmol) and powdered Na2HPO4 (974 mg, 6.86 mmol) in CH2Cl2 (20 mL), and the resulting mixture was stirred at room temperature for 3.5 h. Cold aqueous Na2SO3 (50 mL of 10%) was added, and the mixture was extracted with CH2Cl2 (3×50 mL). The extracts were sequentially washed with cold aqueous Na2SO3 (50 mL of 10%), aqueous NaHCO3 (50 mL) and brine (50 mL). The combined extracts were then evaporated to dryness and the residue was chromatographed on silica gel. Elution with 25% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 25-33% CH2Cl2/petroleum ether gave 2-{[4-(benzyloxy)phenoxy]methyl}-2-methyloxirane (95) (460 mg, 87%) as a white solid: mp (CH2Cl2/pentane) 105-107° C.; 1H NMR (CDCl3) δ 7.44-7.28 (m, 5H), 6.90 (dt, J=9.3, 2.9 Hz, 2H), 6.85 (dt, J=9.3, 2.9 Hz, 2H), 5.01 (s, 2H), 3.97 (d, J=10.5 Hz, 1H), 3.90 (d, J=10.5 Hz, 1H), 2.85 (d, J=4.8 Hz, 1H), 2.71 (d, J=4.8 Hz, 1H), 1.47 (s, 3H). Anal. (C17H18O3) C, H, N.

Provenance & Evidence