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

HRID 463281Notes

Reaction equation

HRID 463281 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:20])[CH2:12][CH2:13][CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[OH:20][CH:11]([C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=1)[CH2:12][CH2:13][CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 202824961-[4-(4-t-Butylphenyl)butan-4-onyl]imidazole

Product 1

HCID 134573631-[4-Hydroxy-4-(4-t-butylphenyl)butyl]imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 5.0 g of the above ketone in 150 ml. of anhydrous methanol was added excess sodium borohydride and the mixture stirred for one 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-t-butylphenyl)butyl]imidazole, which was converted to the oxalate salt and recrystallized from ethyl acetate/ethanol, m.p. 205°-207° C.(foaming).

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-ac368a735b4f46a5a7d9f55a361b33df
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

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