Potassium Carbonate → 3-Phenylbenzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1186705

Reaktionsgleichung

Reaktionsgleichung von HRID 1186705
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.[SH:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:10]1([C:8]2[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[S:16][C:17]=2[C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 676502-Fluorobenzophenone

Produkt 1

HCID 227635043-Phenylbenzo[b]thiophene-2-carboxylic acid methyl esterAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirring solution of (2-fluorophenyl)(phenyl)methanone 87 (2 g, 9.99 mmol) and methyl 2-mercaptoacetate in DMF (30 mL) was added potassium carbonate (4.14 g, 30.0 mmol) and the reaction mixture was stirred at 70° C. for 16 h. The solvent was removed under reduced pressure and the resulting residue was diluted with ethyl acetate and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford methyl 3-phenylbenzo[b]thiophene-2-carboxylate 88 as a white oily solid (0.62 g, 23% yield) after purification by ISCO (0 to 40% ethyl acetate in hexane). LRMS (ESI): (calc) 268.33 (found) 269.156 (MH)+

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-230ec06c43ee4cfe8bc693c3daad4eb5
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673911B2

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