Reaktion #1854127

Reaktionsgleichung

phosphate

methyl 3-(bromomethyl)-2-thenoate

sodium acetate

→

title compound

Ausbeute 79.0%

Methyl 3-(acetoxymethyl)-2thenoate

Ausbeute 79.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at 40° C. for 1 hour
2. 2
   Extraktionthe product was extracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed three times with water
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Vorschrift

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.).

Quelle