Glycidol → HCID 86650541, compound

Participants

Reaction Steps

A mixture of glycidol (115) (303 mg, 4.09 mmol) and 4-(trifluoromethoxy)benzyl bromide (0.810 mL, 5.06 mmol) in anhydrous DMF (6 mL) under N2 at 0° C. was treated with 60% NaH (246 mg, 6.15 mmol), then quickly degassed and resealed under N2. After stirring at room temperature for 7 h, the mixture was cooled (CO2/acetone), quenched with ice/aqueous NaHCO3 (20 mL), added to water (100 mL) and extracted with EtOAc (4×100 mL). The extracts were washed with brine (100 mL) and evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-5% Et2O/petroleum ether firstly gave foreruns, and then further elution with 5-10% Et2O/petroleum ether gave 2-({[4-(trifluoromethoxy)benzyl]oxy}methyl)oxirane (116) (625 mg, 62%) as an oil; 1H NMR (CDCl3) δ 7.38 (dt, J=8.7, 2.3 Hz, 2H), 7.20 (br dd, J=8.7, 0.7 Hz, 2H), 4.62 (d, J=12.0 Hz, 1H), 4.56 (d, J=12.0 Hz, 1H), 3.82 (dd, J=11.5, 2.8 Hz, 1H), 3.43 (dd, J=11.5, 6.0 Hz, 1H), 3.21 (m, 1H), 2.82 (dd, J=4.9, 4.2 Hz, 1H), 2.63 (dd, J=5.0, 2.7 Hz, 1H); HRESIMS calcd for C11H11F3NaO3 m/z [M+Na]+ 271.0552. found 271.0557.

Provenance & Evidence