反応 #2467983

反応方程式

sodium methoxide

dimethyl 3-thiahexanedioate

HCl

→

oil

収率 39.0%

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

収率 39.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度at reflux for 2 h
3. 3
   workup.ADDITIONpoured into ice cold water
4. 4
   抽出The solution was extracted with chloroform
5. 5
   洗浄the combined chloroform layer was washed with water, brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過The solution was filtered
8. 8
   その他evaporated the solvent
9. 9
   その他The residue was chromatographed over silica gel column

実験手順

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%).

出典