Реакция #2467983

Уравнение реакции

sodium methoxide

dimethyl 3-thiahexanedioate

HCl

→

oil

Выход 39.0%

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

Выход 39.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was heated
2. 2
   Температураat reflux for 2 h
3. 3
   workup.ADDITIONpoured into ice cold water
4. 4
   ЭкстракцияThe solution was extracted with chloroform
5. 5
   Промывкаthe combined chloroform layer was washed with water, brine
6. 6
   Сушкаdried over sodium sulfate
7. 7
   ФильтрацияThe solution was filtered
8. 8
   Другоеevaporated the solvent
9. 9
   ДругоеThe residue was chromatographed over silica gel column

Методика

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%).

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