7-[(Trifluoromethylsulfonyl)oxy]-3-phenymethylene-benzopyran-4-one → 7-[(Trifluoromethylsulfonyl)oxy]-3-phenylmethyl-benzopyran-4-one

HRID 1078696Notes

Reaction equation

HRID 1078696 reaction equation
[F:1][C:2]([F:26])([F:25])[S:3]([O:6][C:7]1[CH:24]=[CH:23][C:10]2[C:11](=[O:22])[C:12](=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13][O:14][C:9]=2[CH:8]=1)(=[O:5])=[O:4].[H][H]>C(OCC)(=O)C.[Pd]>[F:26][C:2]([F:1])([F:25])[S:3]([O:6][C:7]1[CH:24]=[CH:23][C:10]2[C:11](=[O:22])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][O:14][C:9]=2[CH:8]=1)(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 538759587-[(Trifluoromethylsulfonyl)oxy]-3-phenymethylene-benzopyran-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 153472507-[(Trifluoromethylsulfonyl)oxy]-3-phenylmethyl-benzopyran-4-oneYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of step D (26.6 g, 69.2 mmole) in 250 mL of ethyl acetate in a 500 mL Parr shaker flask was added 10% palladium on carbon catalyst (1.3 g). The mixture was hydrogenated at 40 psi until hydrogen uptake ceased after about 3 hours. The mixture was filtered through celite (a tradename for diatamaceous earth) to remove the palladium catalyst, and chromatographed over silica gel (hexane-ether); 25.1 g (94% yield) of the title product was obtained

Workup

  1. filtrationThe mixture was filtered through celite (a tradename for diatamaceous earth)
  2. customto remove the palladium catalyst
  3. customchromatographed over silica gel (hexane-ether)

Sources & evidence

ORD record
ord-6511f40f221c4e1fb1ab5de2dc87df42
Source dataset
uspto-grants-1996_08
Patent number
US05550152

Reaction notes

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