4-[1-Cycloheptyl-methylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione → 4-Cycloheptylmethyl-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

HRID 1631891Notes

Reaction equation

HRID 1631891 reaction equation
[CH:1]1([CH:8]=[C:9]2[CH2:13][C:12](=[O:14])[CH:11]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:10]2=[O:24])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:8][CH:9]2[CH2:13][C:12](=[O:14])[CH:11]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:10]2=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 668683574-[1-Cycloheptyl-methylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

Product 1

HCID 668847164-Cycloheptylmethyl-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dioneYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 5% w/w Pd/C (5 mg) was added a solution of 4-[1-Cycloheptyl-methylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (39 mg, 0.12 mmol) in MeOH (10 ml). The reaction was stirred under an atmosphere of H2 (1.5 bar) for 2 hours, filtered through a pad of celite and washed through with MeOH (20 ml). The solvent was removed under reduced pressure to give the desired product as a colourless oil (29 mg) without need for further purification.

Workup

  1. filtrationfiltered through a pad of celite
  2. washwashed through with MeOH (20 ml)
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8211cbb109b04d19a6860ff7e4f4f4a2
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

Loading…