Methallyl alcohol → HCID 66955648, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl-2-propen-1-ol (120) (2.34 mL, 27.8 mmol) in anhydrous DMF (10 mL, then 2×2 mL to rinse) was added to a suspension of 60% NaH (1.32 g, 33.1 mmol) in anhydrous DMF (10 mL) under N2 at 0° C. and the mixture was stirred at 0° C. for 30 min. 4-(Trifluoromethoxy)benzyl bromide (5.1 mL, 31.9 mmol) was added and the mixture was stirred at room temperature for 21 h. The resulting mixture was added to ice/aqueous NaHCO3 (200 mL) and extracted with 25% EtOAc/petroleum ether (2×200 mL) and 50% EtOAc/petroleum ether (3×200 mL). The extracts were washed with water (200 mL), the volatile solvents were removed, and the residual oil was chromatographed on silica gel. Elution with petroleum ether firstly gave foreruns, then further elution with 0-15% CH2Cl2/petroleum ether gave 1-{[(2-methyl-2-propenyl)oxy]methyl}-4-(trifluoromethoxy)benzene (121) (6.57 g, 96%) as an oil that was used directly in the next step; 1H NMR (CDCl3) δ 7.37 (dt, J=8.7, 2.3 Hz, 2H), 7.19 (br d, J=8.0 Hz, 2H), 5.00 (m, 1H), 4.94 (m, 1H), 4.48 (s, 2H), 3.94 (s, 2H), 1.77 (s, 3H).

Provenance & Evidence