4-Toluenesulfonyl chloride → HCID 23157443, compound

HRID 507955Notes

Reaction equation

HRID 507955 reaction equation
[F:1][C:2]([F:19])([CH:8]([OH:18])[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]([F:19])([CH:8]([O:18][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27])[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 23157603HCID 23157603, compound

Product 1

HCID 23157443HCID 23157443, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2,2-difluoro-3-hydroxy-3-(4-nitrophenyl)propanoate (800 mg, 2.91 mmol) in pyridine (20 mL) was added dropwise p-toluenesulfonyl chloride (665 mg, 3.49 mmol), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane) to give the title compound (1.09 g, yield 99%) as a colorless oil.

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e1d50ac50a44420fb258d0714f9c27b5
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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