Ethanol → 2-(4-Hydroxy-2,6-dimethylphenyl)-3-methoxy-5-(tetrahydropyran-4-ylmethyl)cyclopent-2-enone

HRID 1193039Notes

Reaction equation

HRID 1193039 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[C:17](=[O:23])[CH2:18][CH2:19][C:20]=2[O:21][CH3:22])=[C:11]([CH3:24])[CH:10]=1)C1C=CC=CC=1.[H][H].[CH2:27]([OH:29])[CH3:28]>[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH3:24])[C:12]([C:16]2[C:17](=[O:23])[CH:18]([CH2:14][CH:9]3[CH2:10][CH2:11][O:29][CH2:27][CH2:28]3)[CH2:19][C:20]=2[O:21][CH3:22])=[C:13]([CH3:15])[CH:14]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 580708252-(4-Benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enoneHCID 178418361HCID 178418361, compound

Product 1

HCID 580708682-(4-Hydroxy-2,6-dimethylphenyl)-3-methoxy-5-(tetrahydropyran-4-ylmethyl)cyclopent-2-enone

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 2-(4-benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone (1.50 g, 3.59 mmol) in ethanol (10 ml) is added 5% palladium on carbon (0.150 g), and the suspension is stirred for 4 hours under a 4 bar hydrogen atmosphere. The reaction mixture is then filtered through diatomaceous earth, and the filtrate is concentrated in vacuo then purified by flash column chromatography to afford 2-(4-hydroxy-2,6-dimethylphenyl)-3-methoxy-5-(tetrahydropyran-4-ylmethyl)cyclopent-2-enone.

Workup

  1. filtrationThe reaction mixture is then filtered through diatomaceous earth
  2. concentrationthe filtrate is concentrated in vacuo
  3. customthen purified by flash column chromatography

Sources & evidence

ORD record
ord-70218f7c75fe4540ae21c8c9da5a1691
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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