Hydrochloric Acid → 2,2-Difluoro-4-phenylbutan-1-ol

HRID 1280757Notes

Reaction equation

HRID 1280757 reaction equation
C([O:3][C:4](=O)[C:5]([F:15])([F:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[BH4-].[Na+].Cl>CCO.O>[F:14][C:5]([F:15])([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][OH:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 19983613Benzenebutanoic acid, alpha,alpha-difluoro-, ethyl ester

Product 1

HCID 184257752,2-Difluoro-4-phenylbutan-1-olYield 59.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,2-Difluoro-4-phenyl-butyric acid ethyl ester (0.23 g, 1 mmol) was dissolved in EtOH (4 ml) and treated with NaBH4 (39.4 mg, 1 mmol). After 30 minutes stirring at room temperature, the reaction mixture was cooled to 0° C., acidified to pH 1 with 1N HCl (2 ml), diluted with H2O (10 ml). The aqueous phase was extracted with ether (3 times). The combined organic phases were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed over silica gel (hexane-ethylacetate 99:1) to provide 2,2-difluoro-4-phenyl-butan-1-ol (0.11 g, 58%) as light yellow oil, MS: m/e=186.1 (M+).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. extractionThe aqueous phase was extracted with ether (3 times)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed over silica gel (hexane-ethylacetate 99:1)

Sources & evidence

ORD record
ord-cf6f67d6b8154b2285136586da13fee9
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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