HCID 57598852, compound → HCID 178505690, compound

HRID 726498Notes

Reaction equation

HRID 726498 reaction equation
[CH2:1]1[O:24][C:4]2([CH2:9][CH2:8][CH:7]([CH:10]3[CH2:15][CH2:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=4[F:23])=[CH:12][CH2:11]3)[CH2:6][CH2:5]2)[O:3][CH2:2]1>O1CCCC1>[CH2:2]1[O:3][C:4]2([CH2:9][CH2:8][CH:7]([C@H:10]3[CH2:11][CH2:12][C@H:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=4[F:23])[CH2:14][CH2:15]3)[CH2:6][CH2:5]2)[O:24][CH2:1]1

Participants

3

Reactant 1

HCID 57598852HCID 57598852, compound

Product 1

HCID 178505690HCID 178505690, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

First, 5.8 g of 4-[4-(2,3-difluorophenyl)-3-cyclohexenyl]cyclohexanone ethylene ketal, 0.5 g of 10% Pd--C, and 20 ml of tetrahydrofuran were placed in a 200 ml autoclave. The mixture was stirred at room temperature overnight under a hydrogen pressure of 5 kg/cm2. A catalyst was filtered away and a filtrate was distilled away. Thereafter, 25 ml of dry dimethyl sulfoxide and 2.4 g of potassium t-butoxide were added to the residue. The mixture was stirred at room temperature for 4 hours in the atmosphere of argon. Diluted hydrochlolic acid was added to the reaction mixture, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled away to obtain 5.85 g of 4-[trans-4-(2,3-difluorophenyl)cyclohexyl]cyclohexanone ethylene ketal (Y: 75.3%). The compound thus obtained had a purity of 74.9% by GC.

Workup

  1. filtrationA catalyst was filtered away
  2. distillationa filtrate was distilled away
  3. additionThereafter, 25 ml of dry dimethyl sulfoxide and 2.4 g of potassium t-butoxide were added to the residue
  4. stirringThe mixture was stirred at room temperature for 4 hours in the atmosphere of argon
  5. additionDiluted hydrochlolic acid
  6. additionwas added to the reaction mixture
  7. extractionan organic layer was extracted with ether
  8. washThe ether layer was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-f763c777121c406ebf7f72be4710fac4
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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