Acetonitrile → 3-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile

HRID 1917887노트

반응식

HRID 1917887 반응식
[H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]1([C:8](OC)=[O:9])[CH2:7][CH2:6]1.[C:14](#[N:16])[CH3:15]>C1COCC1>[O:9]=[C:8]([C:5]1([C:4]([F:13])([F:12])[F:3])[CH2:7][CH2:6]1)[CH2:15][C:14]#[N:16]

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 242087841-(Trifluoromethyl)cyclopropane-1-carboxylic acid methyl ester

생성물 1

HCID 668764113-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile수율 49.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a slurry of NaH (432 mg, 18 mmol) in THF (40 mL) heated at reflux was added dropwise over 10 minutes a solution of methyl 1-(trifluoromethyl)cyclopropanecarboxylate (2.0 g, 11.9 mmol) in acetonitrile (940 uL, 12 mmol) and the mixture heated at reflux overnight. After cooling to room temperature, the reaction was partitioned between ether and H2O, the aqueous layer acidified with 1N HCl(aq), extracted with ether, and the combined org layers washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (5-40% EtOAc/hexanes) to give 3-oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile (1.04 g, 5.88 mmol, 49%). LC-MS (ESI) m/z 178 (M+H)+.

후처리

  1. temperatureat reflux
  2. temperaturethe mixture heated
  3. temperatureat reflux overnight
  4. customthe reaction was partitioned between ether and H2O
  5. extractionextracted with ether
  6. washthe combined org layers washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by column chromatography (5-40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-19d3b1c10fa0486bbc92a4e0051e67e9
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618289B2

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