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

HRID 2384918Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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]−.

Workup

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

Sources & evidence

ORD record: ord-ffd4d478ae6644b2b84712df8b8b4db2
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263772B2

Reaction notes

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