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

HRID 1533045Notes

Reaction equation

HRID 1533045 reaction equation
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]

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent2×HCID 30318Osmium TetroxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a237b24aa83742d59ac19c5fdbe2a620
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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