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

HRID 844584Notes

Reaction equation

HRID 844584 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[CH2:10][CH:11]=C)[CH:5]=[CH:6][C:7]=1[Cl:8].I([O-])(=O)(=O)=[O:20].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.Cl.C1(C)C=CC=CC=1.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[CH2:10][CH:11]=[O:20])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 23667635Sodium periodateHCID 544025344(S)-(3,4-dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene

Product 1

HCID 544333793(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-alYield 89.9%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent2×

Procedure

4(S)-(3,4-Dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene (4.75 g) (see Preparation 95) was dissolved in a mixture of acetonitrile (75 ml), water (13ml) and 1N aqueous hydrochloric acid solution ( 17 ml). Osmium tetroxide (3.4 ml of a 0.05M solution in toluene) was added and the mixture stirred for 20 minutes. Sodium periodate (5.3 g) was then added together with a further quantity of acetonitrile (30 ml) and stirring continued overnight. Water (ca. 100 ml) was added and the acetonitrile removed under reduced pressure to give an aqueous suspension which was basified to pH>7 by the addition of solid sodium carbonate. The mixture was then extracted (three times) with ethyl acetate and the combined organic extracts washed sequentially with water and brine before being dried over anhydrous sodium sulphate. Removal of the solvent under reduced pressure gave 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-al (4.3 g) as an oil.

Workup

  1. stirringstirring continued overnight
  2. customthe acetonitrile removed under reduced pressure
  3. customto give an aqueous suspension which
  4. extractionThe mixture was then extracted (three times) with ethyl acetate
  5. washthe combined organic extracts washed sequentially with water and brine
  6. dry with materialbefore being dried over anhydrous sodium sulphate
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-034d5fadd4fa418e9a5166233ca800c6
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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