Water → HCID 18467047, compound

HRID 2229252Notes

Reaction equation

HRID 2229252 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=[CH:2]1.[BH4-].[Na+].O>CO>[N:1]1([CH2:6][CH2:7][CH2:8][CH:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[OH:10])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 18467051HCID 18467051, compound

Product 1

HCID 18467047HCID 18467047, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(1H-imidazol-1-yl)-1-(2-naphthyl)-1-butanone (0.793 g) in MeOH (5 ml) was added NaBH4 (0.213 g) and the mixture was stirred at room temperature for 2 hours. Water was added and the whole was concentrated. The residue was extracted with ethyl acetate. The extract was washed with water and brine, dried and concentrated. The residue was chromatographed on silica gel (ethyl acetate-MeOH=20:1) followed by crystallization to give the titled compound (0.615 g) as a colorless solid.

Workup

  1. concentrationthe whole was concentrated
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (ethyl acetate-MeOH=20:1)
  7. customfollowed by crystallization

Sources & evidence

ORD record
ord-22a70d55e8e44e44bc1fecabb038976a
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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