Rac-5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one → 5-Cyclopentyl-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzyl]-2,3-dihydro-4H-chromen-4-one

HRID 1516710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516710
[C:1]1([C:6]2[C:15]([CH:16](O)[C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[C:14]([CH:28]([CH3:30])[CH3:29])[CH:13]=[C:12]3[C:7]=2[C:8](=[O:33])[CH2:9][C:10]([CH3:32])([CH3:31])[O:11]3)[CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)C.[Pd]>[CH:1]1([C:6]2[C:15]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=3)=[C:14]([CH:28]([CH3:29])[CH3:30])[CH:13]=[C:12]3[C:7]=2[C:8](=[O:33])[CH2:9][C:10]([CH3:31])([CH3:32])[O:11]3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 1

HCID 58002986Rac-5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

Produkt 1

HCID 580030055-Cyclopentyl-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzyl]-2,3-dihydro-4H-chromen-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 60 mg (130 μmol) of 5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]-methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 36A) and 14 mg of palladium-on-carbon (10%) in 10 ml of ethanol is stirred under a hydrogen atmosphere at atmospheric pressure overnight. The suspension is filtered through Celite, the filter cake is washed with ethanol and the solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 40:1).

Aufarbeitung

  1. filtrationThe suspension is filtered through Celite
  2. washthe filter cake is washed with ethanol
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 40:1)

Quellen und Nachweise

ORD-Eintrag
ord-8903ec2f7e7a47dbb366a0fc4c331d4c
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227511B2

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