2-(4-Bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)-methylidene]-cyclopentane-1,3-dione → 2-(4-Bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

HRID 514202Notes

Reaction equation

HRID 514202 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[C:12](=[CH:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11][C:10]2=[O:22])=[C:4]([CH3:23])[CH:3]=1.[H][H]>CO.[C].[Pt]>[Br:1][C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11][C:10]2=[O:22])=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

HCID 671097292-(4-Bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)-methylidene]-cyclopentane-1,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 584814642-(4-Bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(4-bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)methylidene]cyclopentane-1,3-dione (0.10 g, 0.26 mmol) in methanol (100 ml) is passed over a cartridge of 10% platinum carbon under a 20 bar hydrogen atmosphere. The reaction mixture is then concentrated in vacuo, and the crude product is purified by flash column chromatography (hexane/ethyl acetate as eluant) to afford rac-2-(4-bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione.

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo
  2. customthe crude product is purified by flash column chromatography (hexane/ethyl acetate as eluant)

Sources & evidence

ORD record
ord-caf12bb9f8a84b789572a550365430ed
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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