1-Butanol → 2-Methyl-2-octen-1-ol

Participants

Reaction Steps

To 85.6 mg (1.1 mmol) of lithium butoxide prepared from n-butanol and lithium metal, there was added 10 ml of ether under an argon atmosphere and stirred at room temperature. The resulting mixture was cooled to -20° C., and a hexane solution of n-butyllithium (1.2 mmol) was added thereto and stirred. An ether solution of 3-methyl-3,4-epoxybutene-1 (89.9 mg; 1.1 mmol) was added dropwise thereto at -20° C., and after the addition was completed, stirring was effected at -20° C. for 1 hour and at 0° C. for 1 hour, followed by the usual work up to give 2-methyl-2-octen-1-ol in a yield of 74%. The Z/E ratio was 93.1/6.9.

Provenance & Evidence