Water → 1-Iodo-2-(4-methylpent-4-en-1-yl)benzene

Participants

Reaction Steps

To a stirred solution of potassium t-butoxide (7.96 g, 71 mmol) in anhydrous ether (100 ml) under nitrogen, was added methyltriphenylphosphonium bromide (25.6 g, 71 mmol). The yellow mixture was stirred under reflux for 0.5 h, allowed to cool for 10 min, and then a solution of 5-(2-iodophenyl)pentan-2-one (Intermediate 1) (9.3 g, 32.3 mmol) in anhydrous ether (70 ml) was added over 20 min. The reaction mixture was refluxed for 1 h, allowed to cool and then poured onto ice. Ether (100 ml) and water (100 ml) were added and the layers were separated. The aqueous layer was re-extracted with ether (100 ml) and the combined organic layers were washed successively with water (100 ml) and saturated brine (100 ml), dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was treated with heptane (200 ml), solid was filtered off and washed with heptane and the filtrate was evaporated. The oil obtained was purified on a 90 g silica cartridge eluted with heptane to give the title compound as a liquid (8.34 g, 90%).

Provenance & Evidence