Water → 1-(2-formyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one

HRID 611178

反応式

HRID 611178 の反応式
P(Cl)(Cl)(Cl)=O.[O:6]1[C:10]2[CH2:11][N:12]([C:15](=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:13][CH2:14][C:9]=2[CH:8]=[CH:7]1.O.CN(C)[CH:31]=[O:32]>>[CH:31]([C:7]1[O:6][C:10]2[CH2:11][N:12]([C:15](=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:13][CH2:14][C:9]=2[CH:8]=1)=[O:32]

参加物

5

反応物 4

HCID 962WaterHCID 6228Dimethylformamide2 回HCID 24813Phosphorus oxychlorideHCID 196001451-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one

生成物 1

HCID 196000211-(2-formyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one

実験手順

To 30 ml of N,N-dimethylformamide, 0.33 ml (3.6 mmol) of phosphorus oxychloride was added under ice-cooling, followed by stirring at room temperature for 0.5 hours. To this mixture, a solution of 1.064 g (3.578 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one in 20 ml of N,N-dimethylformamide was added, followed by overnight stirring at room temperature. After water was added, the reaction mixture was extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel flush column chromatography (hexane/ethyl acetate=2/1 to 1/1) to yield the desired product.

後処理

  1. temperaturecooling
  2. waitfollowed by overnight
  3. stirringstirring at room temperature
  4. extractionthe reaction mixture was extracted with ethyl acetate 3 times
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting crude product was purified by silica gel
  8. customflush column chromatography (hexane/ethyl acetate=2/1 to 1/1)

出典と根拠

ORDレコード
ord-c9c77a809fa44d22bdb0076e300bbbae
出典データセット
uspto-grants-1999_12
特許番号
US05998433

関連ノート

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