Imidazole → 1-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane

HRID 844568노트

반응식

HRID 844568 반응식
CS(O[CH2:6][CH:7]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)(=O)=O.[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:25]1([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:29]=[CH:28][N:27]=[CH:26]1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 226138361-Methanesulphonyloxy-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane

생성물 1

HCID 226138011-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane수율 32.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-Methanesulphonyloxy-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (10 g) (see Preparation 29), imidazole (2.07 g) and potassium carbonate (7.65 g) were dissolved in anhydrous acetonitrile (50 ml) and heated under reflux under a nitrogen atmosphere for 3 days. The organic solvent was then removed under reduced pressure and the resulting aqueous suspension partitioned between dichloromethane and water. The organic phase was separated, washed sequentially with water and brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure. The crude product was chromatographed on silica gel eluting with 95:5, by volume, dichloromethane:methanol to give 1-(imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (3 g) as an oil and as a mixture of diastereomers.

후처리

  1. temperatureheated
  2. temperatureunder reflux under a nitrogen atmosphere for 3 days
  3. customThe organic solvent was then removed under reduced pressure
  4. customthe resulting aqueous suspension partitioned between dichloromethane and water
  5. customThe organic phase was separated
  6. washwashed sequentially with water and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe solvent removed under reduced pressure
  9. customThe crude product was chromatographed on silica gel eluting with 95:5, by volume, dichloromethane

출처 및 근거

ORD 기록
ord-88e8f54d086141acbddcb8b684560007
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380396B1

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