Sodium borohydride → 1-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-ol

HRID 579762Notes

Reaction equation

HRID 579762 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:10]([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 540228171-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one

Product 1

HCID 917371-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-olYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The II-B isomer (2.9 g, 0.01 mole; m.p. 78°-79° C.) of 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-1-pentene-3-one (Compound No. 1') was dissolved in methanol (50 ml). The isomer was allowed to react with sodium borohydride and then treated in the same manner as in Example 1. The residue obtained was recrystallized from a 1:10 mixture of carbon tetrachloride and n-hexane to obtain 2.2 g (yield 76%) of the I'-B isomer (m.p. 116°-117° C.) of Compound No. 1. The elementary analysis and NMR spectrum of the compound are shown below.

Workup

  1. additiontreated in the same manner as in Example 1
  2. customThe residue obtained
  3. customwas recrystallized from a 1:10 mixture of carbon tetrachloride and n-hexane

Sources & evidence

ORD record
ord-7a7f2cee2fc549bfbf18dd02b205e1b5
Source dataset
uspto-grants-1988_06
Patent number
US04749716

Reaction notes

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