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

HRID 1191088노트

반응식

HRID 1191088 반응식
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]

참가 물질

4

반응물 1

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

생성물 1

HCID 231037476-Acetylnicotinonitrile수율 65%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-043f941978734a08bbbf6fdd381112ed
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680091B2

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