Hydrochloric Acid → 1-(2,4-Dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(imidazol-1-yl)-2-butanol hydrochloride

HRID 904651Notes

Reaction equation

HRID 904651 reaction equation
Cl.[Cl:2][C:3]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:4]=1[O:5][CH:6]([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)[C:7](=[O:13])[C:8]([CH3:12])([CH3:11])[CH2:9][F:10].[BH4-].[Na+].Cl>CO>[ClH:2].[Cl:2][C:3]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:4]=1[O:5][CH:6]([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)[CH:7]([OH:13])[C:8]([CH3:12])([CH3:11])[CH2:9][F:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 204785051-(2,4-Dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(imidazol-1-yl)-2-butanone hydrochloride

Product 1

HCID 204785091-(2,4-Dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(imidazol-1-yl)-2-butanol hydrochlorideYield 115.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

44 g (0.1275 mol) of 1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(imidazol-1-yl)-2-butanone (Example 1) were dissolved in 300 ml of methanol, and 6.3 g of sodium borohydride were added at 0° to 5° C. The mixture was subsequently stirred at room temperature for 15 hours, 60 ml of concentrated hydrochloric acid were added dropwise, whilst cooling with ice, the mixture was stirred at room temperature for 10 hours and the solvent was distilled off under a waterpump vacuum. The residue was taken up in 250 ml of methylene chloride, the methylene chloride mixture was stirred into 500 ml of aqueous, saturated sodium bicarbonate solution, the methylene chloride phase was separated off and washed three times with 100 ml of water each time, the organic phase was dried over sodium sulphate and the solvent was distilled off. The oil which remained was taken up in 200 ml of ether, 50 ml of ethereal hydrochloric acid were added and the solvent was distilled off. 28.2 g (58% of theory) of 1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-1-(imidazol-1-yl)-2-butanol hydrochloride of melting point 184°-210° C. were obtained as a diastereomer mixture.

Workup

  1. temperaturewhilst cooling with ice
  2. stirringthe mixture was stirred at room temperature for 10 hours
  3. distillationthe solvent was distilled off under a waterpump vacuum
  4. stirringthe methylene chloride mixture was stirred into 500 ml of aqueous, saturated sodium bicarbonate solution
  5. customthe methylene chloride phase was separated off
  6. washwashed three times with 100 ml of water each time
  7. dry with materialthe organic phase was dried over sodium sulphate
  8. distillationthe solvent was distilled off
  9. addition50 ml of ethereal hydrochloric acid were added
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-b573175de73545799bf1aeece7f59e99
Source dataset
uspto-grants-1983_12
Patent number
US04419361

Reaction notes

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