Chlorotrimethylsilane → 6-(2-Iodophenyl)-3-hexanone

Participants

Reaction Conditions

Reaction Steps

Lithium chloride (6.6 g, 150 mmole) (dried overnight at 115° C. under vacuum) and copper(I) cyanide (6.72 g, 75 mmole) were stirred with tetrahydrofuran (75 ml) under nitrogen for 10 minutes then cooled to −78° C. A solution of 2-iodobenzyl zinc bromide (150 ml, 0.5M in THF, 75 mmol) was added and the mixture was warmed to −15° C., held at this temperature for 20 min then re-cooled to −78° C. Chlorotrimethylsilane (19.1 ml, 150 mmol) was added followed by a solution of ethyl vinyl ketone (7.4 ml, 74.3 mmol) in tetrahydrofuran (15 ml). The mixture was stirred at −78° C. for 3 hours then warmed to room temperature and stirred for 1 hour before being poured into a mixture of water (400 ml) and ether (400 ml). The aqueous layer was extracted with ether (2×400 ml) and the combined ethereal solutions were washed with brine (2×200 ml), dried over anhydrous magnesium sulphate and evaporated in vacuo to give the title compound as a pale yellow liquid (23 g).

Provenance & Evidence