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

HRID 478674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 478674
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 22037088HCID 22037088, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-677538310c974629ae0fa475284390ac
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642240B2

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