Sodium Bicarbonate → HCID 23157355, compound

HRID 507956Notes

Reaction equation

HRID 507956 reaction equation
[F:1][C:2]([F:29])([CH:8](OS(C1C=CC(C)=CC=1)(=O)=O)[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.[C].[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:2]([F:1])([F:29])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 23157443HCID 23157443, compound

Product 1

HCID 23157355HCID 23157355, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2,2-difluoro-3-{[(4-methylphenyl)sulfonyl]oxy}-3-(4-nitrophenyl)propanoate (1.06 g, 2.80 mmol) in ethyl acetate (30 mL) was added 10% palladium-carbon (50% water-containing product, 0.50 g), and the mixture was stirred at room temperature for 16 hr under a hydrogen atmosphere (balloon pressure). To the reaction mixture was added saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-50% ethyl acetate/hexane) to give the title compound (255 mg, yield 40%) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (10%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-581339a6e4174b71a6f651c065d7952a
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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