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

HRID 1592787Notes

Reaction equation

HRID 1592787 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

Trimethylsilyldiazomethane (11.5 mL) was added drop-wise to a solution of 3,5-bis-(trifluoromethyl)benzoic acid (2 g) in dry toluene (20 mL) and methanol (0.5 mL) previously cooled to 0° C. under a nitrogen atmosphere. The solution was stirred at r.t. for 1 hr, then concentrated in vacuo to give 3,5-bis-(trifluoromethyl)-benzoic acid methyl ester (2 g) as a colourless oil. 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-5dcf146c28b9474bab3ae54299fd4f19
Source dataset
uspto-grants-2007_11
Patent number
USRE039921E1

Reaction notes

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