Isopentyltriphenylphosphonium bromide → 9-Bromo-2-methyl-4-decene

Participants

Reaction Conditions

Reaction Steps

n-Butyl lithium (1.5M solution in hexane 6.8 ml) was added to a stirred suspension of (3-methylbutyl)-triphenylphosphonium bromide (4.1 g) in dry tetrahydrofuran (50 ml) at -60° C. under nitrogen. The dark mixture was stirred for 40 minutes at -70° C. then a solution of 6-bromohexanal (1.8 g) in dry tetrahydrofuran (6 ml) was added. The pale mixture was stirred for a further 1 hour at -70° C. then evaporated under vacuum. The residue was extracted with ether and the extract was evaporated to a pale oil which was chromatographed on silica gel, eluting with 1:1 ether:hexane, to give the title compound as a colourless oil. MS M+ 232/234.

Provenance & Evidence