Water → 4-(1-Dimethylcarbamoylmethyl-cyclohex-2-enyl)-butyric acid

HRID 1363999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363999
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:19].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C=O)C>[CH3:17][N:15]([CH3:16])[C:13]([CH2:12][C:6]1([CH2:5][CH2:4][CH2:3][C:2]([OH:19])=[O:1])[CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]1)=[O:14]

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 669367501-(4-hydroxybutyl)-cyclohex-2-enyl-N,N-dimethyl-acetamide

Produkt 1

HCID 669366734-(1-Dimethylcarbamoylmethyl-cyclohex-2-enyl)-butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the relevant 2-[1-(4-hydroxybutyl)-cyclohex-2-enyl]-N,N-dimethyl-acetamide isomer (6) or (6′) (13.7 g, 57.1 mmol) in DMF (200 mL) was added pyridinium dichromate (65.3 g, 241.0 mmol) and the mixture stirred at room temperature for 24 hours. The reaction mixture was poured into H2O (200 mL) and extracted with EtOAc (5×). The combined organic layers were washed with a saturated NaCl solution and dried over anhydrous MgSO4. The solvent was removed in vacuo, the residual DMF was removed by vacuum distillation (Kugelrohr-type) to afford 13.3 g of the desired product which was used without further purification.

Aufarbeitung

  1. extractionextracted with EtOAc (5×)
  2. washThe combined organic layers were washed with a saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe residual DMF was removed by vacuum distillation (Kugelrohr-type)

Quellen und Nachweise

ORD-Eintrag
ord-9d8d87cec3984e658196c9eed9e5ffb8
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888338B2

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