Triethylamine → HCID 20591127, compound

To a 100-mL three-necked flask, 3.41 g of 2-hydroxymethyl-1,3-dithiane, which had been synthesized in accordance with the method known in the art (see Tetrahedron Letters, 41, 5653-5657 (2000)) using 2-carboethoxy-1,3-dithiane as a starting material, and 2.3 g of triethyl amine were added, and to this mixture 40 mL of dried methylene chloride were added and the resulting mixture was stirred with a stirrer bar coated with Teflon™ at 0° C. under nitrogen atmosphere. To the mixture, 2.3 g of methacryloyl chloride was slowly added through a dropping funnel, and the resulting mixture was reacted at 0° C. for 2 hours, and the temperature of the mixture was allowed to return to room temperature, followed by reacting for another 2 hours. After confirming consumption 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 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 yield 3.64 g of 1,3-dithianylmethyl methacrylate (a dithiane derivative of the following formula 2) (yield: 79.4%).

1. additionwere added
2. customthe resulting mixture was reacted at 0° C. for 2 hours
3. customto return to room temperature
4. customconsumption of the starting material by a thin layer chromatography (TLC)
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-dd4e55f539e44d7fb1ccfadb33e50dd3

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349536B2