Sodium Iodide → hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone

Participants

Reaction Steps

Sodium iodide (3 g) is added to a solution of 1 g of 2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} in 20 ml of acetonitrile. The resultant red solution is stirred at room temperature and 2.5 ml of trimethylsilyl chloride is added. After 7.5 hours, water is added, followed by a saturated aqueous sodium thiosulfate solution. The solvent is removed under vacuum, leaving a light yellow oil. Chromatography on silica gel leaves pure 2-(5-hydroxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone}.

Provenance & Evidence