Methanesulfonic Acid → Methyl(4-fluoro-6-methoxy-1-benzothiophen-3-yl)acetate

HRID 591561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591561
S(O)(C)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([S:15][CH2:16][C:17](=O)[CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1>O>[CH3:22][O:21][C:19](=[O:20])[CH2:18][C:17]1[C:8]2[C:7]([F:6])=[CH:12][C:11]([O:13][CH3:14])=[CH:10][C:9]=2[S:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 6395Methanesulfonic AcidHCID 89768091Methyl 4-((3-fluoro-5-methoxyphenyl)sulfanyl)-3-oxobutanoate

Produkt 1

HCID 125474287Methyl(4-fluoro-6-methoxy-1-benzothiophen-3-yl)acetateAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

MsOH (13.68 mL) was added dropwise to methyl 4-((3-fluoro-5-methoxyphenyl)sulfanyl)-3-oxobutanoate (2.87 g) at 0° C. The mixture was stirred at 0° C. for 30 min. The mixture was poured into iced water and extracted with EtOAc. The organic layer was separated, washed successively with water, saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (900 mg).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water, saturated aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-64e057bd6688444b9a8cb568ede9e004
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238639B2

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