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

HRID 1280757ノート

反応式

HRID 1280757 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 184257752,2-Difluoro-4-phenylbutan-1-ol収率 59.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-cf6f67d6b8154b2285136586da13fee9
出典データセット
uspto-grants-2002_09
特許番号
US06451819B2

反応ノート

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