Reaktion #502061

Reaktionsgleichung

4-hydroxytetrahydrothiopyran

triethyl amine

methacryloyl chloride

→

tetrahydro-2H-thiopyran-4-yl methacrylate

Ausbeute 61.3%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 200-mL three-necked flask fitted with a stirrer bar
2. 2
   Sonstigethe resulted mixture was reacted at 0° C. for 40 minutes
3. 3
   Temperaturto warm to room temperature
4. 4
   Sonstigewas further reacted for another 5 hours
5. 5
   workup.ADDITIONthe reaction solution was poured into a 300-mL separatory funnel
6. 6
   Waschenwashed with 100 mL of water
7. 7
   Trocknendried with anhydrous sodium sulfate
8. 8
   SonstigeFrom the obtained solution, the solvent was removed by an evaporator
9. 9
   Sonstigeto obtain an oily crude product
10. 10
    SonstigeThe crude product was purified by silica gel chromatography

Vorschrift

To a 200-mL three-necked flask fitted with a stirrer bar coated with Teflon™, were added 5.37 g of 4-hydroxytetrahydrothiopyran (manufactured by SANKYO KASEI Co., Ltd.), 5.08 g of triethyl amine, and 50 mL of dried methylene chloride, and the mixture was stirred under nitrogen atmosphere at 0° C. To the mixture, 5.0 g of methacryloyl chloride was slowly added through a dropping funnel, and the resulted mixture was reacted at 0° C. for 40 minutes, allowed to warm to room temperature, and was further reacted for another 5 hours. After confirming loss of the starting material by a thin layer chromatography (TLC), the reaction solution was poured into a 300-mL separatory funnel, washed with 100 mL of water followed by 100 mL of saturated NaCl solution (brine), and dried with anhydrous sodium sulfate. From the obtained solution, the solvent was removed by an evaporator, to obtain an oily crude product. The crude product was purified by silica gel chromatography using a mixed solution of n-hexane and ethyl acetate to give 5.18 g of tetrahydro-2H-thiopyran-4-yl methacrylate (thiopyran derivative of the following formula 2) (yield: 61.3%).

Quelle