반응 #502062

반응 방정식

4-hydroxy-4-methyltetrahydrothiopyran

triethyl amine

methacryloyl chloride

→

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

수율 65.3%

용매

methylene chloride

반응 조건

후처리

1. 1
   기타To a 200-mL three-necked flask fitted with a stirrer bar
2. 2
   기타the resulted mixture was reacted at 0° C. for 30 minutes
3. 3
   온도to warm to room temperature
4. 4
   기타was further reacted for another 5 hours
5. 5
   workup.ADDITIONthe reaction solution was poured in a 300-mL separatory funnel
6. 6
   세척washed with 100 mL of water
7. 7
   건조dried with anhydrous sodium sulfate
8. 8
   기타From the obtained solution, the solvent was removed by an evaporator
9. 9
   기타to obtain an oily crude product
10. 10
    기타The crude product was purified by silica gel chromatography

실험 절차

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%).

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