Water → HCID 68999415, compound

Participants

Reaction Steps

A solution of 81.4 g of 2-methyl-8-phenyl-1,2-dihydrobenzo[b]cyclopenta[d]thiophenone (0.29 mol) (1a) in 800 ml of THF was admixed at 0° C. with 225 ml of a 1.0 molar solution of lithium aluminum hydride (0.23 mol) in diethyl ether. The mixture was stirred at room temperature for another 4 hours. 25 ml of water were then carefully added and the resulting suspension was filtered through a layer of Celite and dried over magnesium sulfate. After filtration, the solvent was removed and a brown vitreous solid was obtained. The solid was dissolved in 400 ml of toluene and, after addition of 2.0 g of p-toluenesulfonic acid, stirred at 70° C. for 2 hours. The cooled reaction mixture was washed with a saturated solution of sodium hydrogencarbonate and with water and dried over magnesium sulfate. After the desiccant had been separated off, the solvent was removed and the residue was chromatographed on silica gel (5% methylene chloride in hexane as eluant). This gave 39 g (52%) of (1b) as a light-yellow oil.

Provenance & Evidence