Ethyl Acetate → 2-(4-Chloro-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-3a,7a-dihydro-6H-thieno[2,3-c]pyridin-7-one

HRID 2384918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384918
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:36][CH:11]3[C:12](=[O:35])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([O:22][Si](C(C)C)(C(C)C)C(C)C)=[C:18]([O:33][CH3:34])[CH:17]=4)[CH:14]=[CH:15][CH:10]3[CH:9]=2)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:36][CH:11]3[C:12](=[O:35])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:33][CH3:34])[CH:17]=4)[CH:14]=[CH:15][CH:10]3[CH:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 689537112-(4-chloro-phenyl)-6-(3-methoxy-4-triisopropylsilanyloxy-phenyl)-3a,7a-dihydro-6H-thieno[2,3-c]pyridin-7-one

Produkt 1

HCID 689502812-(4-Chloro-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-3a,7a-dihydro-6H-thieno[2,3-c]pyridin-7-oneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolve 2-(4-chloro-phenyl)-6-(3-methoxy-4-triisopropylsilanyloxy-phenyl)-3a,7 a-dihydro-6H-thieno[2,3-c]pyridin-7-one (2.86 g, 5.29 mmol) in THF (55 mL), cool to 0° C., and treat with 1.0 M TBAF (5.8 mL, 5.8 mmol). Stir the reaction at 0° C. for 10 min and at RT for 2 h. Dilute the reaction with EtOAc (150 mL), wash with saturated NH4Cl (100 mL), water (100 mL), and brine (100 mL). Dry the organic portion over Na2SO4, filter, and concentrate. Wash the resulting crude material with refluxing hexanes (2×40 mL) and dry in vacuo to give 1.95 g (96%) of the title compound. LC-MS/ES m/z (35Cl) 384.0 [M−H]−.

Aufarbeitung

  1. customthe reaction at 0° C. for 10 min
  2. additionDilute
  3. washwash with saturated NH4Cl (100 mL), water (100 mL), and brine (100 mL)
  4. dry with materialDry the organic portion over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. washWash the resulting crude material with refluxing hexanes (2×40 mL)
  8. customdry in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ffd4d478ae6644b2b84712df8b8b4db2
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263772B2

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