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

HRID 1533050ノート

反応式

HRID 1533050 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bdf7dfbc8bd34fa2b93a99d182bce818
出典データセット
uspto-grants-2001_03
特許番号
US06207678B1

反応ノート

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