Hydrochloric Acid → HCID 12848952, compound

HRID 2296334Notes

Reaction equation

HRID 2296334 reaction equation
[F:1][CH2:2][C:3]([CH2:24][F:25])([CH3:23])[C:4](=[O:22])[CH:5]([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[BH4-].[Na+].Cl>CO>[F:1][CH2:2][C:3]([CH2:24][F:25])([CH3:23])[CH:4]([OH:22])[CH:5]([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:15])[F:16])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 12848950HCID 12848950, compound

Product 1

HCID 12848952HCID 12848952, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

63.7 g (0.176 mole) of 3,3-bisfluoromethyl-1-(imidazol-1-yl)-1-(3-trifluoromethylphenoxy)-butan-2-one (obtained as described in Example 1) were dissolved in 250 ml of methanol, and 3 g (0.08 mole) of sodium borohydride were added in portions. The reaction solution was subsequently stirred for 1 hour and was 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. 44.5 g (70% of theory) of 3,3-bisfluoromethyl-1-(imidazol-1-yl)-1-(3-trifluoromethylphenoxy)-butan-2-ol of melting point 107°-20° 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

Sources & evidence

ORD record
ord-ccfa6641a2124cb3ba23e0835a838286
Source dataset
uspto-grants-1984_01
Patent number
US04428949

Reaction notes

Loading…