Dichloromethane → 3-[(Allyloxy)methyl]-3-ethyloxetane

Participants

Reaction Conditions

Reaction Steps

To a solution of 23.2 g (0.2 mol) of 3-ethyl-3-hydroxymethyloxetane in 48.4 g (0.4 mol) of allylbromide and 50 g of a 50 wt % aqueous solution of potassium hydroxide in a 300 mL round bottom flask equipped with a magnetic stirrer was added 1.0 g of tetra-n-butylammonium bromide with vigorous stirring at 0° C. After 24 hrs, 100 mL of dichlorometane and 100 mL of water were added to the reaction mixture. The organic phase was washed with water twice, dried over magnesium sulfate, filtered and the solvent removed on a rotary evaporator. The residue was purified by distillation under vacuum, giving 28.6 g of 3-ethyl-3-allyloxymethyloxetane (yield 92%, b.p.:55° C. at 1.5 mm Hg).

Provenance & Evidence