4-Coumaric acid → HCID 11288952, compound

4-hydroxy-cinnamic acid (4.21 g, 25.67 mmol) and imidazole (5.24 g, 77.01 mmol) were charged in a 250 mL round-bottom flask and dissolved in 25 mL of dimethylformamide. Tert-butyldimethylsilyl chloride (8.12 g, 83.90 mmol) was added thereto at 0° C., followed by stirring for 30 minutes. 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 (114 mL)/methanol (322 mL), and a 0.00035M potassium carbonate aqueous solution (120 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 (114 mL)/methanol (322 mL)
9. additiona 0.00035M potassium carbonate aqueous solution (120 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 record

ord-db7d84694bb24562a21b2183f815684e

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637674B2