Reacción #2467983

Ecuación de reacción

sodium methoxide

dimethyl 3-thiahexanedioate

HCl

→

oil

Rendimiento 39.0%

Methyl 4-oxo-2,3,5-trihydrothiophene-3-carboxylate

Rendimiento 39.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was heated
2. 2
   Temperaturaat reflux for 2 h
3. 3
   workup.ADDITIONpoured into ice cold water
4. 4
   ExtracciónThe solution was extracted with chloroform
5. 5
   Lavadothe combined chloroform layer was washed with water, brine
6. 6
   Secadodried over sodium sulfate
7. 7
   FiltraciónThe solution was filtered
8. 8
   Otroevaporated the solvent
9. 9
   OtroThe residue was chromatographed over silica gel column

Procedimiento

To a stirred slurry of sodium methoxide (1.68 g, 31.25 mmol) in dry THF (15 mL) was added a solution of dimethyl 3-thiahexanedioate (5 g, 26.03 mmol) in THF (10 mL) at rt for 5 min. The reaction mixture was heated at reflux for 2 h, cooled to rt and poured into ice cold water and acidified with dil. HCl. The solution was extracted with chloroform and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-EtOAc (95:5) as eluents to give the product as pale yellow color oil (1.6 g, 39%).

Fuente