Ethyl Acetate → Methyl 5-fluoro-1-benzothiophene-2-carboxylate

HRID 1843957

Reaktionsgleichung

Reaktionsgleichung von HRID 1843957
[SH:1][CH2:2][C:3]([O:5][CH3:6])=[O:4].F[C:8]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:9]=1[CH:10]=O.C(OCC)(=O)C>CC#N.CCCCCC>[F:16][C:13]1[CH:14]=[CH:15][C:8]2[S:1][C:2]([C:3]([O:5][CH3:6])=[O:4])=[CH:10][C:9]=2[CH:12]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 16907Methyl ThioglycolateHCID 1376632,5-Difluorobenzaldehyde

Produkt 1

HCID 22473847Methyl 5-fluoro-1-benzothiophene-2-carboxylateAusbeute 33,89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

TEA (3.705 g, 36.619 mmol) was added to a solution of methyl 2-mercaptoacetate (3.293 g, 30.985 mmol) in CH3CN (12.5 mL). This was followed by the addition of 2,5-difluorobenzaldehyde (4 g, 28.169 mmol) in CH3CN (12.5 mL) and the resulting reaction mass was refluxed overnight under nitrogen atmosphere. The reaction was monitored by TLC (5% ethyl acetate in hexane). The reaction mass was concentrated under reduced pressure to obtain the crude product. Purification by column chromatography on silica gel (15% ethyl acetate in hexane) afforded 2 g of the product (33.89% yield).

Aufarbeitung

  1. customthe resulting reaction mass
  2. temperaturewas refluxed overnight under nitrogen atmosphere
  3. concentrationThe reaction mass was concentrated under reduced pressure
  4. customto obtain the crude product
  5. customPurification by column chromatography on silica gel (15% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5e0a56d21a124533abfb1ce61d0ba034
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946260B2

Verknüpfte Notizen

Wird geladen…