Sodium hydride → (E)-ethyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)-2-methylacrylate

HRID 632641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632641
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[C:19]1[C:20]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:21]=2[S:22](=[O:32])[C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>CN(C=O)C>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:20]2[C:19]([O:1][C:2]3[CH:3]=[CH:4][C:5](/[CH:8]=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=3)=[C:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[S:22](=[O:32])[C:21]=2[CH:33]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 14920484(E)-ethyl 3-(4-hydroxyphenyl)-2-methylacrylateHCID 159594683-Bromo-6-methoxy-2-(4-methoxyphenyl)benzothiophene 1-oxide

Produkt 1

HCID 86730657(E)-ethyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)-2-methylacrylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of (E)-ethyl 3-(4-hydroxyphenyl)-2-methylacrylate (92 mg, 0.445 mmol) in DMF (2.0 mL) was added sodium hydride (60% suspension in oil, 17.79 mg, 0.445 mmol), the resulting mixture was allowed to stir for 30 min at room temperature. To the solution was added 3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (125 mg, 0.342 mmol) as a suspension in DMF (2.0 mL). The reaction was heated to 80° C. for 15 h. Upon completion the reaction was cooled to room temperature, quenched with water and extracted with EtOAc. The combined organic layers were then washed with water, sat. aq. NaHCO3, brine and then collected (phase separator) and concentrated in vacuo to afford the crude product. The crude material was purified by column chromatography (SiO2, 0-70% EtOAc/Heptane) to afford (E)-ethyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)-2-methylacrylate (144 mg, 0.294 mmol, 86% yield). LC/MS (m/z, MH+): 491.3

Aufarbeitung

  1. temperatureThe reaction was heated to 80° C. for 15 h
  2. temperatureUpon completion the reaction was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were then washed with water, sat. aq. NaHCO3, brine
  6. customcollected (phase separator)
  7. concentrationconcentrated in vacuo
  8. customto afford the crude product
  9. customThe crude material was purified by column chromatography (SiO2, 0-70% EtOAc/Heptane)

Quellen und Nachweise

ORD-Eintrag
ord-28ee9397bb4a42cc81db213b80fe361d
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321746B2

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