Potassium Carbonate → HCID 2779414, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-trifluoromethoxyphenol (0.152 mL, 1.17 mmol), K2CO3 (260 mg, 1.17 mmol) and 2-(bromomethyl)oxirane (76) (0.30 mL, 3.51 mmol) in anhydrous acetone (3 mL) was stirred in a sealed vial at 59° C. for 36 h. The resulting mixture was filtered, washing with CH2Cl2, and then the filtrate was evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-15% CH2Cl2/pentane firstly gave foreruns, and then further elution with 20-25% CH2Cl2/pentane gave 2-{[4-(trifluoromethoxy)phenoxy]methyl}oxirane (77) (similarly prepared by Cao et al., WO 2008112483A2 using epichlorohydrin) (260 mg, 95%) as an oil; 1H NMR (CDCl3) δ 7.14 (br dd, J=9.0, 0.6 Hz, 2H), 6.91 (dt, J=9.1, 3.0 Hz, 2H), 4.23 (dd, J=11.1, 3.1 Hz, 1H), 3.94 (dd, J=11.1, 5.7 Hz, 1H), 3.34 (m, 1H), 2.91 (dd, J=4.8, 4.2 Hz, 1H), 2.75 (dd, J=4.9, 2.6 Hz, 1H).

Provenance & Evidence