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

HRID 1583706Notes

Reaction equation

HRID 1583706 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-3ad7115174c8471c840cb8acf064ba2a
Source dataset
uspto-grants-1985_11
Patent number
US04554007

Reaction notes

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