Tetrahydrofuran → HCID 54070568, compound

Participants

Reaction Conditions

Reaction Steps

Lithium diisopropylamide (40 mL of 1.5M solution, 60 mmol) was added to a solution of N-ethylidenecyclohexanamine (30 mL of 2M solution, 60 mmol) in tetrahydrofuran at -10° C. After stirring for 30 minutes and further cooling to -50° C., 2-cyclohexyl-3,3-bis(4-fluorophenyl)propenal (8.4 g, 25.8 mmol) was added and the solution stirred for 3 hours during which time it was allowed to warm to 20° C. The solution was quenched with 2N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried with magnesium sulfate and concentrated in vacuo. The residue was stirred for 4 days with a mixture of 100 mL benzene, 60 mL acetic acid and 40 mL water. The mixture was diluted with an additional 100 mL water and the layers separated. The organic phase was washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo. The residue was cyrstallized from hexane to give 6.0 g of the title compound; m.p. =116°-118° C.

Provenance & Evidence