Reaction #1854127

Reaction equation

phosphate

methyl 3-(bromomethyl)-2-thenoate

sodium acetate

→

title compound

Yield 79.0%

Methyl 3-(acetoxymethyl)-2thenoate

Yield 79.0%

Solvents

N,N-dimethylformamide

Conditions

Workup

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

Procedure

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.).

Source