Sodium borohydride → 1-[4-Hydroxy-4-(4-chlorophenyl)butyl]imidazole

HRID 442510Notes

Reaction equation

HRID 442510 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[OH:17][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190783351-[4-(4-Chlorophenyl)butan-4-onyl]imidazole

Product 1

HCID 203652141-[4-Hydroxy-4-(4-chlorophenyl)butyl]imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 5 g. of the above ketone in 150 ml. of anhydrous methanol was added excess sodium borohydride, and the mixture stirred for 1 hour. After removal of the solvent, a small quantity of water was added and the mixture was extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and evaporated to afford 1-[4-hydroxy-4-(4-chlorophenyl)butyl]imidazole.

Workup

  1. customTo a 0° C.
  2. customAfter removal of the solvent
  3. additiona small quantity of water was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-a9be0da4478146a18dbc13aa49ae9732
Source dataset
uspto-grants-1977_08
Patent number
US04045568

Reaction notes

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