6-(1-Ethoxy-vinyl)-nicotinonitrile → 6-Acetylnicotinonitrile

HRID 1191088ノート

反応式

HRID 1191088 の反応式
C([O:3][C:4]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)=[CH2:5])C>C1COCC1.Cl>[C:4]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)(=[O:3])[CH3:5]

参加物

4

反応物 1

HCID 598289076-(1-Ethoxy-vinyl)-nicotinonitrile

生成物 1

HCID 231037476-Acetylnicotinonitrile収率 65%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Dissolve crude 6-(1-ethoxy-vinyl)-nicotinonitrile (14.5 g, ca. 80%) in THF (120 mL) and 2.5 N hydrochloric acid (40 mL). Stir the solution for 16 h at room temperature. Quench the reaction with saturated aqueous NaHCO3 (pH to 7.5). Extract the mixture with EtOAc (200 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (120 g) eluting with hexane/EtOAc (9:1 to 3:1 gradient) to obtain the desired intermediate (4.2 g, 65%).

後処理

  1. customQuench
  2. customthe reaction with saturated aqueous NaHCO3 (pH to 7.5)
  3. extractionExtract the mixture with EtOAc (200 mL)
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the crude mixture by chromatography on silica gel (120 g)
  8. washeluting with hexane/EtOAc (9:1 to 3:1 gradient)

出典と根拠

ORDレコード
ord-043f941978734a08bbbf6fdd381112ed
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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