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

HRID 11878

反応式

HRID 11878 の反応式
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]

参加物

5

反応物 3

HCID 9794Ethyl trifluoroacetateHCID 142862-AcetylpyridineHCID 10942334Sodium Methoxide

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-041f2cc851b84257b82bcd81cc91efb6
出典データセット
uspto-grants-2006_08
特許番号
US07098335B2

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