Reaction #2467983

Reaction equation

sodium methoxide

dimethyl 3-thiahexanedioate

HCl

→

oil

Yield 39.0%

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

Yield 39.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated
2. 2
   Temperatureat reflux for 2 h
3. 3
   workup.ADDITIONpoured into ice cold water
4. 4
   ExtractionThe solution was extracted with chloroform
5. 5
   Washthe combined chloroform layer was washed with water, brine
6. 6
   Dryingdried over sodium sulfate
7. 7
   FiltrationThe solution was filtered
8. 8
   Otherevaporated the solvent
9. 9
   OtherThe residue was chromatographed over silica gel column

Procedure

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%).

Source