Hydrochloric Acid → HCID 9927503, compound

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Reaction Steps

3.5 g (500 mmol) of lithium are added to a suspension of 25.4 g (165 mmol) of titanium trichloride in 300 ml of 1,2-dimethoxyethane. The mixture is refluxed for 2 hours and then cooled to room temperature. A solution of 7.5 g (27 mmol) of 4-fluoro-4'-methylsulfonylbenzophenone, prepared in Example 2, and 2.25 g (27 mmol) of cyclopentanone in 80 ml of 1,2-dimethoxyethane is added dropwise and the mixture is refluxed for 8 hours. After cooling, the mixture is treated with dilute hydrochloric acid solution and extracted with t-butyl methyl ether. The organic phase is dried over magnesium sulfate and evaporated under vacuum to give a residue, which is chromatographed on silica gel in dichloromethane. The resulting oil crystallizes from an isopropyl ether/pentane mixture to give 4 g of 4-[(cyclopentylidene)(4-fluorophenyl)methyl]methylsulfonylbenzene in the form of crystals melting at 84°-85° C.

Provenance & Evidence