Water → 1-(4-Chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylthio-butan-2-ol

HRID 1249149Notes

Reaction equation

HRID 1249149 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH:7]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[C:8](=[O:17])[C:9]([CH3:16])([S:11][C:12]([F:15])([F:14])[F:13])[CH3:10])=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH:8]([OH:17])[C:9]([CH3:16])([S:11][C:12]([F:13])([F:15])[F:14])[CH3:10])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 131173041-(4-Chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylthio-butan-2-one

Product 1

HCID 131173051-(4-Chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylthio-butan-2-olYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 g (0.026 mol) of 1-(4-chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylthio-butan-2-one (Example 1) were dissolved in 100 ml of methanol and 1 g (0.025 mol) of sodium borohydride was added in portions to the solution. The reaction mixture was further stirred at room temperature for 30 minutes and was thereafter introduced into water. The mixture was extracted with methylene chloride, and the organic phase was dried over sodium sulphate and concentrated in vacuo. The residue crystallized after a short time. 9.5 g (95% of theory) of 1-(4-chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylthio-butan-2-ol of melting point 85°-87° C. were obtained.

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. dry with materialthe organic phase was dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue crystallized after a short time

Sources & evidence

ORD record
ord-76e139ba46db43b5ad4f7d7e7e5c91e1
Source dataset
uspto-grants-1986_12
Patent number
US04629732

Reaction notes

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