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3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → (2E)-3-{4-[(tert-butyldimethylsilyl)oxy]-3-methoxyphenyl}prop-2-enoic acid

HRID 476205
Notes
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Reaction equation

HRID 476205 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 11185931(2E)-3-{4-[(tert-butyldimethylsilyl)oxy]-3-methoxyphenyl}prop-2-enoic acid

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.

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

Sources & evidence

ORD record
ord-9708da531eec436384af84a96007e043
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637674B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes