反応 #502062

反応方程式

4-hydroxy-4-methyltetrahydrothiopyran

triethyl amine

methacryloyl chloride

→

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

収率 65.3%

溶媒

methylene chloride

反応条件

後処理

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

実験手順

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%).

出典