HCID 67109729, compound → HCID 58481464, compound

HRID 509171Notes

Reaction equation

HRID 509171 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 67109729HCID 67109729, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58481464HCID 58481464, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(4-bromo-2,6-dimethylphenyl)-4-[1-(tetrahydropyran-4-yl)-methylidene]-cyclopentane-1,3-dione (0.1 g, 0.26 mmol) in methanol (100 ml) is subjected to hydrogenation under H-Cube conditions using 10% platinum carbon under a 20 bar hydrogen atmosphere. The reaction mixture is then concentrated to give a crude product which is purified by flash chromatography (hexane/ethyl acetate) to afford 2-(4-bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione (0.09 g).

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. customto give a crude product which
  3. customis purified by flash chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d6d03e2721b041abab3a6e61e12f5b64
Source dataset
uspto-grants-2015_08
Patent number
US09096560B2

Reaction notes

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