3,5-Dimethylcyclohex-2-en-1-one → AG-G-83630

HRID 1417029

Reaction equation

HRID 1417029 reaction equation
[CH3:1][C:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][C:4](=[O:9])[CH:3]=1>CC(O)C.[Pd].CCCCCC>[CH3:1][C@H:2]1[CH2:7][C@@H:6]([CH3:8])[CH2:5][C:4](=[O:9])[CH2:3]1

Participants

5

Reactant 1

HCID 142913,5-Dimethylcyclohex-2-en-1-one

Product 1

HCID 642498AG-G-83630Yield 76.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 8058HexaneSolvent

Procedure

A solution of 3,5-dimethyl-2-cyclohexenone (2.0 g, 16.1 mmol) in 2-propanol (32 ml) was hydrogenated over 5% palladium on charcoal (200 mg) at room temperature and 103 kPa (14.7 psi) for 4 hours, then diluted with 1:1 hexane:ether (150 ml) and filtered using a filter aid. The filtrate was evaporated under reduced pressure to provided the substantially stereochemically pure title compound (1.56 g) as a yellow oil. 13C NMR spectroscopy revealed a cis:trans ratio of 150:3.

Workup

  1. filtrationether (150 ml) and filtered
  2. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-30328e82970d457ba6e7b820a9129582
Source dataset
uspto-grants-1999_06
Patent number
US05917034

Linked notes

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