Diethyl Ether → HCID 10942917, compound

Participants

Reaction Conditions

Reaction Steps

μ-Chloro-μ-methylene[bis(cyclopentadienyl)titanium]dimethylaluminum (172 mL, 0.086 mol, 0.5 M in toluene) is added dropwise to a solution of 4-phenylcyclohexanone (15.0 g, 0.086 mol) in THF (100 mL) at 0° C. The mixture is allowed to come to 25° C. After 15 min., ether (100 mL) is added followed by dropwise addition of 0.1 M sodium hydroxide (120 mL). The mixture is stirred an 25° C. for 18 h, filtered, and the filtrate is dried over sodium sulfate and concentrated in vacuo . The residue is purified by column chromatography on silica gel using dichloromethane-hexanes (1:1) as eluent. The resulting yellow oil is rechromatographed using hexanes as eluent to give 8.9 g (61%) of 4-phenyl-1-methylenecyclohexane as an oil.

Provenance & Evidence