Tetrahydrofuran → HCID 10955105, compound

Participants

Reaction Steps

To a stirred and cooled THF (400 ml) solution of the (E)-1,1-dibromo-6-methyl-1,5-pentadecadiene (6) (37.0 g, 97.6 mmols), an n-hexane solution of n-BuLi (1.5 M, 150 ml, 225 mmols) was added dropwise at −70° C. under an Ar gas. The mixture was stirred for 1 hour at −70° C. and for 1.5 hours at room temperature. Then, the reaction mixture was poured into 1.5 liters of ice water, and extracted with n-hexane. The hexane solution was washed with water, dried with sodium sulfate, and concentrated in a vacuum. The residue was subjected to silica gel column chromatography, and eluted with n-hexane to obtain 18.9 g (88.0%) of (E)-6-methyl-5-pentadecen-1-yne (7) as oily matter.

Provenance & Evidence