7-Cyclopent-3-en-1-yl-5-methoxy-2,2-dimethyl-4-oxochroman-6-carbaldehyde → HCID 58003009, compound

HRID 1516684Notes

Reaction equation

HRID 1516684 reaction equation
[CH:1]1([C:6]2[CH:15]=[C:14]3[C:9]([C:10](=[O:18])[CH2:11][C:12]([CH3:17])([CH3:16])[O:13]3)=[C:8]([O:19][CH3:20])[C:7]=2[CH:21]=[O:22])[CH2:5][CH2:4][CH:3]=[CH:2]1.C1(C2C=C3C(C(=O)CC(C)(C)O3)=C(OC)C=2C=O)CC=CC1.[H][H]>C(OCC)(=O)C.[Pd]>[CH:1]1([C:6]2[CH:15]=[C:14]3[C:9]([C:10](=[O:18])[CH2:11][C:12]([CH3:17])([CH3:16])[O:13]3)=[C:8]([O:19][CH3:20])[C:7]=2[CH:21]=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 580029407-Cyclopent-3-en-1-yl-5-methoxy-2,2-dimethyl-4-oxochroman-6-carbaldehydeHCID 580029507-Cyclopent-2-en-1-yl-5-methoxy-2,2-dimethyl-4-oxochroman-6-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 58003009HCID 58003009, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under argon, 3.3 g (11 mmol) of the mixture of 7-cyclopent-2-en-1-yl-5-methoxy-2,2-dimethyl-4-oxochroman-6-carbaldehyde and 7-cyclopent-3-en-1-yl-5-methoxy-2,2-dimethyl-4-oxochroman-6-carbaldehyde (Example 4A/5A) are dissolved in 200 ml of ethyl acetate, 500 mg of palladium-on-carbon (10%) are added and hydrogen gas is charged at room temperature under atmospheric pressure. After one hour, the mixture is filtered through a layer of silica gel, the filter cake is washed thoroughly with ethyl acetate and the filtrate is concentrated. This gives 3.3 g (99% of theory) of the title compound.

Workup

  1. filtrationthe mixture is filtered through a layer of silica gel
  2. washthe filter cake is washed thoroughly with ethyl acetate
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-fa1f1d34467d49beba08509165d3179f
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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