HCID 58002993, compound → 7-Cyclopentyl-5-methoxy-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one

HRID 1516686Notes

Reaction equation

HRID 1516686 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]([OH:32])[C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>ClCCl.[O-2].[Mn+4].[O-2]>[CH:1]1([C:6]2[CH:15]=[C:14]3[C:9]([C:10](=[O:18])[CH2:11][C:12]([CH3:16])([CH3:17])[O:13]3)=[C:8]([O:19][CH3:20])[C:7]=2[C:21](=[O:32])[C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 58002993HCID 58002993, compound

Product 1

HCID 580029777-Cyclopentyl-5-methoxy-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

100 mg (0.22 mmol) of 7-cyclopentyl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-5-methoxy-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 7A) are dissolved in 5 ml of dichloromethane, 194 mg (2.23 mmol) of manganese(IV) oxide are added and the mixture is stirred at room temperature overnight. The mixture is filtered through a layer of silica gel, the filter cake is washed thoroughly with ethyl acetate and the filtrate is concentrated to dryness. The crude product is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). This gives 82.5 mg (83% 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 to dryness
  4. customThe crude product is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-35dd085d81bb4878b9cedbcacfcf7574
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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