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

HRID 844563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 844563
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]

Komponenten

8

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel2×HCID 30318Osmium TetroxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c9786ecda2d94162b357383b462a814d
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380396B1

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