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

HRID 2384918ノート

反応式

HRID 2384918 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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]−.

後処理

  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

出典と根拠

ORDレコード
ord-ffd4d478ae6644b2b84712df8b8b4db2
出典データセット
uspto-grants-2012_09
特許番号
US08263772B2

反応ノート

読み込み中…