Sodium Carbonate → 3-(3,4-Dichlorophenyl)-4-(imidazol-1-yl)butan-1-al

HRID 844563ノート

反応式

HRID 844563 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]([CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[CH2:11][CH:12]=C)[CH:6]=[CH:7][C:8]=1[Cl:9].I([O-])(=O)(=O)=[O:21].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.[Os](=O)(=O)(=O)=O.C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]([CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[CH2:11][CH:12]=[O:21])[CH:6]=[CH:7][C:8]=1[Cl:9]

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 226138204-(3,4-Dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene hydrochlorideHCID 23667635Sodium periodate

生成物 1

HCID 226138043-(3,4-Dichlorophenyl)-4-(imidazol-1-yl)butan-1-al収率 71%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒2 回HCID 30318Osmium Tetroxide溶媒

実験手順

4-(3,4-Dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene hydrochloride (3.6 g) (see Preparation 24) was dissolved in a mixture of acetonitrile (50 ml) and water (20 ml) and osmium tetroxide (4 ml of a 0.05M solution in toluene) added. The mixture was stirred for 30 minutes, sodium periodate (5.3 g) added and stirring continued for 2 hours. A further portion of acetonitrile (20 ml) was added and stirring continued for 16 hours before removal of the organic solvent under reduced pressure to give an aqueous suspension. This was basified to pH>7 by the addition of solid sodium carbonate. The mixture was then extracted with dichloromethane, the organic phase dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give a dark oil which was chromatographed on silica gel eluting with a solvent gradient of 98:2 changing to 92.5:7.5, by volume, dichloromethane:methanol to give 3-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-al (2.28 g) as a colourless, viscous oil.

後処理

  1. additionadded
  2. stirringstirring
  3. waitcontinued for 2 hours
  4. stirringstirring
  5. customcontinued for 16 hours before removal of the organic solvent under reduced pressure
  6. customto give an aqueous suspension
  7. extractionThe mixture was then extracted with dichloromethane
  8. dry with materialthe organic phase dried over anhydrous sodium sulphate
  9. customthe solvent removed under reduced pressure
  10. customto give a dark oil which
  11. customwas chromatographed on silica gel eluting with a solvent gradient of 98:2 changing to 92.5:7.5, by volume, dichloromethane

出典と根拠

ORDレコード
ord-c9786ecda2d94162b357383b462a814d
出典データセット
uspto-grants-2002_04
特許番号
US06380396B1

反応ノート

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