Tetrahydrofuran → HCID 54527787, compound

HRID 1086074Notes

Reaction equation

HRID 1086074 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(=NC1CCCCC1)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[C:26]([CH3:29])[CH:27]=O)=[CH:21][CH:20]=1.[O:37]1CC[CH2:39][CH2:38]1>>[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[C:26]([CH3:29])[CH:27]=[CH:39][CH:38]=[O:37])=[CH:23][CH:24]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 10964544N-cyclohexylethanimineHCID 15133052HCID 15133052, compound

Product 1

HCID 54527787HCID 54527787, compound

Procedure

Lithium diisopropylamide (13 mL of 1.84M solution, 24 mmol) was added to N-ethylidenecyclohexanamine (12 mL of 2M solution, 24 mmol) in tetrahydrofuran at -40° C. After stirring for 30 minutes 3,3-bis(4-fluorophenyl)-2-methylpropenal (2.1 g, 8.1 mmol) was added and the solution stirred for 4 hours during which time the temperature was allowed to rise to -15° 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 16 hours with a mixture of 100 mL benzene, 65 mL acetic acid and 35 mL of water. The mixture was diluted to 500 mL with water and the aqueous layer was separated and extracted with diethyl ether. The combined organic solution was washed with saturated sodium bicarbonate and water, 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 after hexane crystallization 1.5 g of the title compound; m.p. =86°-88° C.

Workup

  1. additionwas added
  2. customto rise to -15° 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 16 hours with a mixture of 100 mL benzene, 65 mL acetic acid and 35 mL of water
  8. additionThe mixture was diluted to 500 mL with water
  9. customthe aqueous layer was separated
  10. extractionextracted with diethyl ether
  11. washThe combined organic solution was washed with saturated sodium bicarbonate and water
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by chromatography on silica eluting with 1% ethyl acetate in hexane
  15. customto give
  16. customafter hexane crystallization 1.5 g of the title compound
  17. customm.p. =86°-88° C.

Sources & evidence

ORD record
ord-920248b45f804f0bbe0215ae3108fd62
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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