Dimethylformamide → HCID 23157275, Verbindung

HRID 2110867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110867
[C:1]([C:5]1[CH2:6][C:7](=[O:10])[NH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].CN(C)[CH:31]=[O:32]>O>[C:1]([C:5]1[CH:6]=[C:7]([O:10][CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[N:8]([CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:23]([O:32][CH3:31])=[O:26])=[CH:15][CH:14]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 5204213-tert-butyl-4,5-dihydro-1H-pyrazol-5-one

Produkt 1

HCID 23157275HCID 23157275, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 5-tert-butyl-2,4-dihydro-3H-pyrazol-3-one (5.00 g, 35.7 mmol), methyl 4-(bromomethyl)benzoate (17.16 g, 74.91 mmol), potassium carbonate (10.5 g, 76.0 mmol) and N,N-dimethylformamide (50 mL) was stirred overnight at 60° C. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:3) to give the title compound (6.90 g, yield 44%) as a colorless oil. melting point 93-94° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract washed with aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8081945f9ee743c7bd1622db8e70da6c
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517910B2

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