Tetrahydrofuran → HCID 53866743, compound

Temperature

-50 °C

Lithium diisopropylamide (5.4 mL of 1.84M solution, 10 mmol) was added to N-ethylidenecyclohexanamine (5 mL of 2M solution, 10 mmol) in tetrahydrofuran at -20° C. After stirring for 30 minutes and further cooling to -50° C., 3,3-bis(4-fluorophenyl)-2-(1,1-dimethylethyl)propenal (0.9 g, 3.0 mmol) was added and the solution stirred for 4 hours during which time the temperature was allowed to rise to -20° C. The solution was quenched with 2N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried and concentrated in vacuo. The residue was stirred for 18 hours with a mixture of 50 mL benzene, 15 mL of water and 35 mL of acetic acid. The mixture was diluted to 200 mL with water. The organic layer was separated, washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 1% ethyl acetate in hexane to give 0.5 g of the title compound; m.p. =87°-89° C.

1. stirringthe solution stirred for 4 hours during which time the temperature
2. customto rise to -20° C
3. customThe solution was quenched with 2N hydrochloric acid
4. extractionthe mixture extracted with diethyl ether
5. customThe extracts were dried
6. concentrationconcentrated in vacuo
7. stirringThe residue was stirred for 18 hours with a mixture of 50 mL benzene, 15 mL of water and 35 mL of acetic acid
8. additionThe mixture was diluted to 200 mL with water
9. customThe organic layer was separated
10. washwashed with saturated sodium bicarbonate solution
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated in vacuo
13. customThe residue was purified by chromatography on silica eluting with 1% ethyl acetate in hexane

ORD record

ord-cdf98eaad0cc4b819b732906e08885b2

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05011947