Dimethylformamide → Ethyl 6-methoxybenzo[b]thiophene-2-carboxylate

HRID 1171227

Reaktionsgleichung

Reaktionsgleichung von HRID 1171227
CN(C)C=O.F[C:7]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:8]=1[CH:9]=O.[SH:17][CH2:18][C:19]([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].[C:28](OCC)(=O)[CH3:29]>O>[CH2:28]([O:20][C:19]([C:18]1[S:17][C:7]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:8]=2[CH:9]=1)=[O:21])[CH3:29]

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27348732-Fluoro-4-methoxybenzaldehydeHCID 5086465Acetic acid, mercapto-, ion(1-)

Produkt 1

HCID 11831419Ethyl 6-methoxybenzo[b]thiophene-2-carboxylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To an N,N-dimethylformamide (50 mL) solution of 2-fluoro-4-methoxybenzaldehyde (5.0 g, 32.5 mmol) and 2-mercapto-acetate (3.56 mL, 32.5 mmol) was added potassium carbonate (12.1 g, 87.5 mmol). This mixture was stirred at room temperature for 5 hours. The reaction mixture was distributed between ethyl acetate and water. The organic layer was separated followed by washing with water, drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1 to 10:1) and NH silica gel chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (6.72 g, 88%).

Aufarbeitung

  1. customThe organic layer was separated
  2. washby washing with water
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe resulting residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1 to 10:1) and NH silica gel chromatography (heptane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-4e097e1663ab4403856981b799d8f174
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829585B2

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