Ethyl trifluoroacetate → 4,4,4-Trifluoro-1-(pyridin-2-yl)butane-1,3-dione

HRID 11878

반응식

HRID 11878 반응식
C(O[C:4](=[O:9])[C:5]([F:8])([F:7])[F:6])C.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[O:18])[CH3:17].C[O-].[Na+]>CO>[F:8][C:5]([F:6])([F:7])[C:4](=[O:9])[CH2:17][C:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=1)=[O:18]

참가 물질

5

반응물 3

HCID 9794Ethyl trifluoroacetateHCID 142862-AcetylpyridineHCID 10942334Sodium Methoxide

생성물 1

HCID 27714784,4,4-Trifluoro-1-(pyridin-2-yl)butane-1,3-dione수율 81.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Trifluoro-acetic acid ethyl ester (9.82 mL, 82.5 mmol) was added to a solution of 1-pyridin-2-yl-ethanone (5.00 g, 41.2 mmol) in methanol (40 mL) containing sodium methoxide (61.8 mmol). The reaction mixture was heated at reflux overnight, concentrated under reduced pressure and acidified with aqueous hydrochloric acid (10%). The aqueous solution was extracted with ethyl acetate (10×50 mL). The organic layers were collected, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to give 4,4,4-trifluoro-1-pyridin-2-yl-butane-1,3-dione (7.26 g, 81%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. extractionThe aqueous solution was extracted with ethyl acetate (10×50 mL)
  5. customThe organic layers were collected
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-041f2cc851b84257b82bcd81cc91efb6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098335B2

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