반응 #2467983

반응 방정식

sodium methoxide

dimethyl 3-thiahexanedioate

HCl

→

oil

수율 39.0%

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

수율 39.0%

용매

THF

THF

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for 2 h
3. 3
   workup.ADDITIONpoured into ice cold water
4. 4
   추출The solution was extracted with chloroform
5. 5
   세척the combined chloroform layer was washed with water, brine
6. 6
   건조dried over sodium sulfate
7. 7
   여과The solution was filtered
8. 8
   기타evaporated the solvent
9. 9
   기타The residue was chromatographed over silica gel column

실험 절차

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%).

출처