Hydrochloric Acid → 1-(4-Chlorophenoxy)-4-fluoro-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol

HRID 851129Notes

Reaction equation

HRID 851129 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[C:8](=[O:14])[C:9]([CH3:13])([CH3:12])[CH2:10][F:11])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:8]([OH:14])[C:9]([CH3:12])([CH3:13])[CH2:10][F:11])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 205026601-(4-Chlorophenoxy)-3,3-dimethyl-4-fluoro-1-(1,2,4-triazol-1-yl)-2-butanone

Product 1

HCID 205026621-(4-Chlorophenoxy)-4-fluoro-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-olYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

55 g (0.176 mol) of 1-(4-chlorophenoxy)-4-fluoro-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one (Example 1) were dissolved in 250 ml of methanol, and 3 g (0.08 mol) of sodium borohydride were added in portions. The reaction solution was subsequently stirred for 1 hour and then adjusted to a pH value of 3 with concentrated hydrochloric acid. After distilling off the solvent in vacuo, water was added to the residue and the mixture was extracted by shaking with methylene chloride. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. The residue was crystallized with petroleum ether. 40 g (72% of theory) of 1-(4-chlorophenoxy)-4-fluoro-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of melting point 103°-112° C. were obtained.

Workup

  1. distillationAfter distilling off the solvent in vacuo, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted
  4. stirringby shaking with methylene chloride
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized with petroleum ether

Sources & evidence

ORD record
ord-efaebfe225de4762820ee618a8c2884d
Source dataset
uspto-grants-1983_05
Patent number
US04382944

Reaction notes

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