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

HRID 1363999노트

반응식

HRID 1363999 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9d8d87cec3984e658196c9eed9e5ffb8
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888338B2

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