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Dimethylformamide dimethyl acetal → HCID 67258869、化合物

HRID 2359021
ノート
印刷プレビュー

反応式

HRID 2359021 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:15])[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>CN(C)C=O>[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:15])[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:18][N:19]([CH3:21])[CH3:20])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 65583291HCID 65583291、化合物

生成物 1

HCID 67258869HCID 67258869、化合物収率 53.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 1-(5-chloro-2-thienyl)-2-(pyridin-4-yl)ethanone (21 mmol) in 13 mL N,N-dimethylformamide, was added N,N-dimethylformamide dimethyl acetal (71.5 mmol). The mixture was refluxed for 3 h and then allowed to cool to room temperature. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried over MgSO4 filtered and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol 100:1 to 20:1) to afford 3.3 g (51% yield) of 1-(5-chloro-2-thienyl)-3-(dimethylamino)-2-(pyridin-4-yl)prop-2-en-1-one.

後処理

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol 100:1 to 20:1)

出典と根拠

ORDレコード
ord-91a0bc7bc719400ea9ff771dc2785820
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08685974B2

反応ノート

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