Triethylamine → HCID 59476866, compound

Temperature

0 °C

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%).

1. customTo a 200-mL three-necked flask fitted with a stirrer bar
2. customthe resulted mixture was reacted at 0° C. for 40 minutes
3. temperatureto warm to room temperature
4. customwas further reacted for another 5 hours
5. additionthe reaction solution was poured into a 300-mL separatory funnel
6. washwashed with 100 mL of water
7. dry with materialdried with anhydrous sodium sulfate
8. customFrom the obtained solution, the solvent was removed by an evaporator
9. customto obtain an oily crude product
10. customThe crude product was purified by silica gel chromatography

ORD record

ord-24b26e57378e449b932dc84b3a06d04a

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088556B2