Hydrochloric Acid → 3,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-ol

HRID 1649178Notes

Reaction equation

HRID 1649178 reaction equation
[F:1][CH2:2][C:3]([CH2:21][F:22])([CH3:20])[C:4](=[O:19])[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[F:1][CH2:2][C:3]([CH2:21][F:22])([CH3:20])[CH:4]([OH:19])[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 130194373,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-one

Product 1

HCID 130194383,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-olYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

31.9 g (0.097 mol) of 3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-one were dissolved in 600 ml of methanol, and 5.45 g (0.14 mol) of sodium borohydride were added in portions at 0° to 5° C. The mixture was subsequently stirred for 15 hours, 15 ml of concentrated hydrochloric acid were added and the mixture was stirred at room temperature for 2 hours. Thereafter, the reaction mixture was stirred into 800 ml of aqueous, saturated sodium bicarbonate solution. It was extracted with 1,000 ml of methylene chloride and the organic phase was washed twice with 1,000 ml of water each time, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The oil which remained was stirred with isopropyl ether. 22.2 g (67.5% of theory) of 3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-ol of melting point 137° C. were obtained. ##STR77##

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionIt was extracted with 1,000 ml of methylene chloride
  3. washthe organic phase was washed twice with 1,000 ml of water each time
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. distillationby distilling off the solvent in vacuo
  7. stirringThe oil which remained was stirred with isopropyl ether

Sources & evidence

ORD record
ord-991b89c3282a4cbbaacca3d3d2f14dee
Source dataset
uspto-grants-1983_11
Patent number
US04415586

Reaction notes

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