Sodium borohydride → HCID 13247649, compound

HRID 543329Notes

Reaction equation

HRID 543329 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)=[N:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)=[N:12][CH:13]=2)[OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13247703HCID 13247703, compound

Product 1

HCID 13247649HCID 13247649, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7 g of 5-(4-chlorobenzoyl)-2-(1-imidazolyl)pyridine in 60 ml of ethanol plus 10 ml of water is added 1 g of sodium borohydride. After the mixture is stirred at room temperature for an hour, the solvent is distilled off. To the residue is added water and the mixture is extracted with chloroform. After the chloroform is distilled off, the residue is recrystallized from a mixture of toluene and ethanol to give 6.5 g of α-(4-chlorophenyl)-2-(1-imidazolyl)-5-pyridinemethanol as white crystals, melting at 147°-149° C.

Workup

  1. distillationthe solvent is distilled off
  2. additionTo the residue is added water
  3. extractionthe mixture is extracted with chloroform
  4. distillationAfter the chloroform is distilled off
  5. customthe residue is recrystallized from a mixture of toluene and ethanol

Sources & evidence

ORD record
ord-5ecba5d553a3447fac994d22cfa8ad14
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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