Tetrahydrofuran → HCID 54070568, compound

Temperature

-50 °C

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.

1. stirringthe solution stirred for 3 hours during which time it
2. temperatureto warm to 20° C
3. customThe solution was quenched with 2N hydrochloric acid
4. extractionthe mixture extracted with diethyl ether
5. dry with materialThe extracts were dried with magnesium sulfate
6. concentrationconcentrated in vacuo
7. stirringThe residue was stirred for 4 days with a mixture of 100 mL benzene, 60 mL acetic acid and 40 mL water
8. additionThe mixture was diluted with an additional 100 mL water
9. customthe layers separated
10. washThe organic phase was washed with water and saturated sodium bicarbonate solution
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated in vacuo

ORD record

ord-dd81d345007b4e11b88d7ae8c772240d

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05011947