HCID 19103676, compound → HCID 178447891, compound

HRID 1198316Notes

Reaction equation

HRID 1198316 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH:11]=1>[Pd].C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 19103676HCID 19103676, compound

Product 1

HCID 178447891HCID 178447891, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 10 mmol of 1-(2,3,4-trifluorophenyl)-4-propylcyclohex-1-ene (prepared from 2,3,4-trifluophenyllithium and 4-propylcyclohexanone and subsequent dehydration with p-toluenesulfonic acid), 0.1 g of palladium-on-active charcoal (1%) and 15 ml of toluene is hydrogenated to saturation at room temperature. After filtration and removal of the solvent, the residue is dissolved in 15 ml of dimethyl sulfoxide, 1.2 g of potassium tert.-butanolate are added and the mixture is stirred at room temperature for 2 hours. Acidification and customary working up give trans-1-(2,3,4-trifluorophenyl)-4-propylcyclohexane.

Workup

  1. customis hydrogenated to saturation at room temperature
  2. filtrationAfter filtration and removal of the solvent
  3. dissolutionthe residue is dissolved in 15 ml of dimethyl sulfoxide
  4. addition1.2 g of potassium tert.-butanolate are added

Sources & evidence

ORD record
ord-099508df1e044dfa8caf1543a50efad8
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Reaction notes

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