3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → HCID 11185931, compound

HRID 476207

Reaction equation

HRID 476207 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[OH:14])[CH:6]=[CH:7][C:8]([OH:10])=[O:9].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 7093-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11185931HCID 11185931, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-methoxy-4-hydroxy-cinnamic acid (8 g, 41.2 mmol) and imidazole (8.4 g, 123.6 mmol) were charged in a 500 mL round-bottom flask and dissolved in 30 mL of dimethylformamide. Tert-butyldimethylsilyl chloride (13.04 g, 86.5 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 (200 mL) was added thereto, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate, concentrated and dissolved in tetrahydrofuran (180 mL)/methanol (500 mL), and a 0.00035M potassium carbonate aqueous solution (175 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.

Workup

  1. customat 0° C.
  2. customThe reaction liquid
  3. concentrationwas concentrated by distillation under reduced pressure and dichloromethane (200 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 (180 mL)/methanol (500 mL)
  9. additiona 0.00035M potassium carbonate aqueous solution (175 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

Sources & evidence

ORD record
ord-a791b323335748f0a6cc4abc4ce47047
Source dataset
uspto-grants-2014_01
Patent number
US08637674B2

Linked notes

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