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

HRID 1280757노트

반응식

HRID 1280757 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-cf6f67d6b8154b2285136586da13fee9
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451819B2

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