反应 #502062

反应方程式

4-hydroxy-4-methyltetrahydrothiopyran

triethyl amine

methacryloyl chloride

→

4-methyl-tetrahydro-2H-thiopyran-4-yl methacrylate

收率 65.3%

溶剂

methylene chloride

反应条件

后处理

1. 1
   其他To a 200-mL three-necked flask fitted with a stirrer bar
2. 2
   其他the resulted mixture was reacted at 0° C. for 30 minutes
3. 3
   温度to warm to room temperature
4. 4
   其他was further reacted for another 5 hours
5. 5
   workup.ADDITIONthe reaction solution was poured in a 300-mL separatory funnel
6. 6
   洗涤washed with 100 mL of water
7. 7
   干燥dried with anhydrous sodium sulfate
8. 8
   其他From the obtained solution, the solvent was removed by an evaporator
9. 9
   其他to obtain an oily crude product
10. 10
    其他The crude product was purified by silica gel chromatography

实验过程

To a 200-mL three-necked flask fitted with a stirrer bar coated with Teflon™, were added 5.95 g of 4-hydroxy-4-methyltetrahydrothiopyran (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 30 minutes, allowed to warm to room temperature, and was further reacted for another 5 hours. After confirming loss of the starting material by TLC, the reaction solution was poured in a 300-mL separatory funnel, washed with 100 mL of water followed by with 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 5.89 g of 4-methyl-tetrahydro-2H-thiopyran-4-yl methacrylate (thiopyran derivative of the following formula 3) (yield: 59.4%).

来源