Methallyl alcohol → HCID 10707028, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl-2-propen-1-ol (120) (1.17 mL, 13.9 mmol) in anhydrous DMF (5 mL, then 2×1 mL to rinse) was added to a suspension of 60% NaH (674 mg, 16.9 mmol) in anhydrous DMF (5 mL) under N2 at 0° C. and the mixture was stirred at 0° C. for 30 min. A solution of 4-(benzyloxy)benzyl chloride (3.87 g, 16.6 mmol) in anhydrous DMF (6 mL, then 2×2 mL to rinse) was added and the mixture was stirred at room temperature for 16 h. The resulting mixture was added to ice/aqueous NaHCO3 (100 mL) and extracted with EtOAc (4×100 mL). The extracts were washed with water (100 mL), the EtOAc was removed, and the residual oil was chromatographed on silica gel. Elution with petroleum ether firstly gave foreruns, then further elution with 0-25% CH2Cl2/petroleum ether gave 1-(benzyloxy)-4-{[(2-methyl-2-propenyl)oxy]methyl}benzene (122) (reported by Wennerberg et al., 1999 via alkylation of 4-(benzyloxy)benzyl alcohol) (3.48 g, 93%) as an oil that was used directly in the next step; 1H NMR (CDCl3) δ 7.45-7.28 (m, 5H), 7.27 (dt, J=8.5, 2.4 Hz, 2H), 6.95 (dt, J=8.7, 2.4 Hz, 2H), 5.07 (s, 2H), 4.99 (m, 1H), 4.91 (m, 1H), 4.42 (s, 2H), 3.91 (s, 2H), 1.76 (s, 3H).

Provenance & Evidence