Methyl 4-[4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]benzoate → HCID 22730084, compound

HRID 2085664Notes

Reaction equation

HRID 2085664 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22730509Methyl 4-[4-(1,1-dimethylethyl)-1-cyclohexen-1-yl]benzoate

Product 1

HCID 22730084HCID 22730084, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A room temperature mixture of Example 5B (230 mg, 0.84 mmol) and 10% Pd/C (100 mg) in ethyl acetate (5 mL) was stirred under a hydrogen atmosphere for 3 hours, filtered through a pad of silica gel (10 g) with diethyl ether (10 mL), and concentrated to provide the desired product as a ˜2:1 mixture of diastereomers. MS (DCI) m/e 275 (M+H)+.

Workup

  1. filtrationfiltered through a pad of silica gel (10 g) with diethyl ether (10 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f6af82e6161945c5b9d8934b261be5e9
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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