2-(4-bromo-2,6-dimethyl-phenyl)-4-[1-cyclohexyl-meth-(E)-ylidene]-cyclopentane-1,3-dione → 4-Cyclohexylmethyl-2-(2,6-dimethyl-phenyl)-cyclopentane-1,3-dione

HRID 1631883Notes

Reaction equation

HRID 1631883 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])/[C:12](=[CH:15]/[CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)/[CH2:11][C:10]2=[O:22])=[C:4]([CH3:23])[CH:3]=1>CO.[Pd]>[CH:16]1([CH2:15][CH:12]2[CH2:11][C:10](=[O:22])[CH:9]([C:5]3[C:6]([CH3:8])=[CH:7][CH:2]=[CH:3][C:4]=3[CH3:23])[C:13]2=[O:14])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 1

HCID 668680902-(4-bromo-2,6-dimethyl-phenyl)-4-[1-cyclohexyl-meth-(E)-ylidene]-cyclopentane-1,3-dione

Product 1

HCID 668683764-Cyclohexylmethyl-2-(2,6-dimethyl-phenyl)-cyclopentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(4-bromo-2,6-dimethyl-phenyl)-4-[1-cyclohexyl-meth-(E)-ylidene]-cyclopentane-1,3-dione (250 mg, 0.844 mmol) in methanol (25 ml) was added 10% palladium on carbon (50 mg, 20%) and stirred at room temperature under hydrogen balloon pressure for 7-8 hours. The reaction mixture was filtered through celite bed, concentrated under high vacuum. Compounds were separated by auto prep purification system to give 4-cyclohexylmethyl-2-(2,6-dimethyl-phenyl)-cyclopentane-1,3-dione.

Workup

  1. filtrationThe reaction mixture was filtered through celite bed
  2. concentrationconcentrated under high vacuum
  3. customCompounds were separated by auto prep purification system

Sources & evidence

ORD record
ord-2444549cb1984cafb2be0d36b9418749
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

Loading…