Phosphate → Methyl 3-(acetoxymethyl)-2-thenoate

HRID 1766945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766945
Br[CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9].[C:12]([O-:15])(=[O:14])[CH3:13].[Na+].P([O-])([O-])([O-])=O>CN(C)C=O>[C:12]([O:15][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:14])[CH3:13]

Komponenten

5

Edukt 3

HCID 1061PhosphateHCID 517045Sodium AcetateHCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylate

Produkt 1

HCID 17862579Methyl 3-(acetoxymethyl)-2-thenoateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-(bromomethyl)-2-thenoate (described in Tetrahedron Lett., 22, 5097-5100, (1981); 6.80 g, 28.9 mmol) in N,N-dimethylformamide (80 ml) was added sodium acetate (7.12 g, 86.8 mmol). The mixture was stirred at room temperature for 24 hours, and then stirred at 40° C. for 1 hour. A phosphate buffer solution (pH 7, 100 ml) was added to the reaction mixture, and the product was extracted with ethyl acetate. The organic layer was washed three times with water, and the solvent was distilled off under reduced pressure. The residue was subjected to chromatography on a silica gel (150 g) column (eluent; ethyl acetate:hexane=1:10˜1:1) to afford the title compound (4.89 g, 79% yield) as a colorless solid (mp. 42-43° C.).

Aufarbeitung

  1. stirringstirred at 40° C. for 1 hour
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed three times with water
  4. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aaf5c6314f6e4ddbb5a57827f70da4b5
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230023B2

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