Reaktion #2467983

Reaktionsgleichung

sodium methoxide

dimethyl 3-thiahexanedioate

HCl

→

oil

Ausbeute 39.0%

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

Ausbeute 39.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturat reflux for 2 h
3. 3
   workup.ADDITIONpoured into ice cold water
4. 4
   ExtraktionThe solution was extracted with chloroform
5. 5
   Waschenthe combined chloroform layer was washed with water, brine
6. 6
   Trocknendried over sodium sulfate
7. 7
   FiltrationThe solution was filtered
8. 8
   Sonstigeevaporated the solvent
9. 9
   SonstigeThe residue was chromatographed over silica gel column

Vorschrift

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%).

Quelle