Acetic Anhydride → Methyl 3-(2-acetylthiophen-3-yl)benzoate

HRID 1740295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1740295
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:2]1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([C:2]1[S:1][CH:5]=[CH:4][C:3]=1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:18])[CH3:17]

Komponenten

3

Edukt 2

HCID 7918Acetic AnhydrideHCID 3564198Methyl 3-(3-thienyl)benzoate

Produkt 1

HCID 21838227Methyl 3-(2-acetylthiophen-3-yl)benzoateAusbeute 60,4 %

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of methyl 3-(thiophen-3-yl)benzoate (2 g) in acetic anhydride (2 g) was heated to 75° C. The oil bath was removed and phosphoric acid (0.063 ml) was added thereto. The reaction mixture was stirred at 140° C. for 2 hours and cooled to room temperature. The mixture was diluted with ethyl acetate and washed successively with water, an aqueous sodium carbonate solution (×2) and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane:ethyl acetate (10:1) to afford methyl 3-(2-acetylthiophen-3-yl)benzoate (1.44 g).

Aufarbeitung

  1. customThe oil bath was removed
  2. additionphosphoric acid (0.063 ml) was added
  3. temperaturecooled to room temperature
  4. additionThe mixture was diluted with ethyl acetate
  5. washwashed successively with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane:ethyl acetate (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-3dc5a2ba29db4f0b9a84aeffc7ce342a
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05968985

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