Sodium borohydride → HCID 13247671, compound

HRID 543323Notes

Reaction equation

HRID 543323 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)[C:5]([C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[CH3:15])=[O:6].[BH4-].[Na+]>C(O)C.O>[CH3:13][C:12]1[CH:11]=[C:10]([CH3:14])[CH:9]=[C:8]([CH3:15])[C:7]=1[CH:5]([C:4]1[CH:16]=[CH:17][C:18]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[C:2]([Cl:1])[CH:3]=1)[OH:6]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 20206233HCID 20206233, compound

Product 1

HCID 13247671HCID 13247671, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In 100 ml of ethanol is dissolved 15.6 g of oily 3-chloro-4-(1-imidazolyl)-2',4',6'-trimethylbenzophenone obtained in the reference example 4. To the ethanol solution is added a solution of 1.8 g of sodium borohydride in 20 ml of water. After the whole solution is stirred at 50° C. for 17 hours, the reaction mixture is poured into ice-cold water and extracted with chloroform. The chloroform is distilled off and the residue is recrystallized from toluene to give 14 g of α-(2,4,6-trimethylphenyl)-3-chloro-4-(1-imidazolyl)benzenemethanol as white crystals, melting at 156°-157° C.

Workup

  1. customobtained in the reference example 4
  2. additionthe reaction mixture is poured into ice-cold water
  3. extractionextracted with chloroform
  4. distillationThe chloroform is distilled off
  5. customthe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-684fabbd0b814e2984409b36a8c5174f
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Reaction notes

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