1-Butanol → 2-Methyl-2-dodecen-1-ol

Participants

Reaction Conditions

Reaction Steps

A hexane solution of n-butanol (77.1 mg; 1.0 mmol) was cooled to 0° C. under an argon atmosphere, and a hexane solution of n-butyllithium (1.0 ml) was added dropwise thereto and stirred. To the resulting solution, there was further dropwise added a hexane solution of n-octyllithium (1.2 mmol) and a hexane solution of 3-methyl-3,4-epoxybutene-1 (88.1 mg; 1.0 mmol), and after the addition was completed, the resulting mixture was cooled at 0° C. for 1 hour and at room temperature for 1.5 hours, followed by the usual work up. Removal of the solvent and distillation of the residue gave 150 mg of 2-methyl-2-dodecen-1-ol (yield, 75%; Z/E=93.0/7.0).

Provenance & Evidence