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

HRID 2384918노트

반응식

HRID 2384918 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-ffd4d478ae6644b2b84712df8b8b4db2
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263772B2

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