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

HRID 871486ノート

反応式

HRID 871486 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-8edc404c3ef14dae9e322fbc162103bd
出典データセット
uspto-grants-2015_03
特許番号
US08969587B2

反応ノート

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