Imidazole → (2E)-3-[4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3,5-dimethoxyphenyl]-2-propenoic Acid

3,5-dimethoxy-4-hydroxy-cinnamic acid (3 g, 13.38 mmol) and imidazole (2.73 g, 40.14 mmol) were charged in a 500 mL round-bottom flask and dissolved in 15 mL of dimethylformamide. Tert-butyldimethylsilyl chloride (4.23 g, 28.09 mmol) was added thereto at 0° C., followed by stirring for 1 hour. The reaction liquid was concentrated by distillation under reduced pressure and dichloromethane (50 mL) was added thereto, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate, concentrated and dissolved in tetrahydrofuran (59 mL)/methanol (167 mL), and a 0.00035M potassium carbonate aqueous solution (62 mL) was added thereto, followed by stirring for 1 hour. After being concentrated by distillation under reduced pressure, the resulting solid was filtered, washed with water, and dried under vacuum to afford the title compound.

1. customat 0° C.
2. customThe reaction liquid
3. concentrationwas concentrated by distillation under reduced pressure and dichloromethane (50 mL)
4. additionwas added
5. washby washing with water
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. concentrationconcentrated
8. dissolutiondissolved in tetrahydrofuran (59 mL)/methanol (167 mL)
9. additiona 0.00035M potassium carbonate aqueous solution (62 mL) was added
10. stirringby stirring for 1 hour
11. concentrationAfter being concentrated by distillation under reduced pressure
12. filtrationthe resulting solid was filtered
13. washwashed with water
14. customdried under vacuum

ORDレコード

ord-b800385a77a142f0b475b7e246260dbe

出典データセット

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08637674B2