[I-].[Na+].C[O:4][CH:5]([CH2:19][CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:17][CH2:16][CH:15]2[CH:11]1[CH2:12][C:13](=[O:18])[CH2:14]2.C[Si](Cl)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[OH:4][CH:5]([CH2:19][CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:17][CH2:16][CH:15]2[CH:11]1[CH2:12][C:13](=[O:18])[CH2:14]2Sodium 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}.
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