N-vinyl-2-pyrrolidone → HCID 22037088, compound

HRID 1864086Notes

Reaction equation

HRID 1864086 reaction equation
CO[C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1.[CH:19]([N:21]1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26])=[CH2:20].[H-].[Na+]>C1(C)C=CC=CC=1>[F:16][C:14]([F:17])([F:15])[C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:7]=1)[C:3]([CH:23]1[CH2:24][CH2:25][N:21]([CH:19]=[CH2:20])[C:22]1=[O:26])=[O:18]

Participants

5

Reactant 3

HCID 6917N-vinyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 141265Methyl 3,5-di(trifluoromethyl)benzoate radical

Product 1

HCID 22037088HCID 22037088, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3,5-bis-(trifluoromethyl)-benzoic acid methyl ester (2 g) and 1-vinyl-2-pyrrolidinone (863 μL) was added to a mixture of sodium hydride (60% suspension in mineral oil-0.41 g) in dry toluene (30 mL) previously heated to reflux. The mixture was stirred for 12 hrs, then it was partitioned between saturated ammonium chloride solution and AcOEt. The organic layer was dried, concentrated in vacuo and the residue was purified by flash chromatography (CH/AcOEt 8:2) to give the title compound (1.6 g) as a beige oil.

Workup

  1. temperaturepreviously heated to reflux
  2. customit was partitioned between saturated ammonium chloride solution and AcOEt
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by flash chromatography (CH/AcOEt 8:2)

Sources & evidence

ORD record
ord-3434c941d5154236a8ef735b6f09246a
Source dataset
uspto-grants-2009_12
Patent number
US07625904B2

Reaction notes

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