Imidazole → HCID 57890276, compound

HRID 2367653Notes

Reaction equation

HRID 2367653 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[C:20](=[O:21])[C:19]3[C:14](=[C:15]([CH3:26])[C:16]([O:22]C(=O)C)=[CH:17][CH:18]=3)[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].N1C=CN=C1.O>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[C:20](=[O:21])[C:19]3[C:14](=[C:15]([CH3:26])[C:16]([OH:22])=[CH:17][CH:18]=3)[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 57890263HCID 57890263, compound

Product 1

HCID 57890276HCID 57890276, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetic acid 3-(3,4-dimethoxy-phenyl)-8-methyl-4-oxo-chroman-7-yl ester (1.1 g, 3.2 mmol) and imidazole (3.2 g, 47 mmol) were refluxed in EtOH (100 ml). The reaction was complete after 90 minutes and allowed to cool to room temperature before pouring into stirred H2O (800 ml). A fine white precipitate was filtered off and 1H NMR in d-CDCl3 indicated the solid was 3-(3,4-Dimethoxy-phenyl)-7-hydroxy-8-methyl-chroman-4-one in >95% purity (0.31 g, 30%).

Workup

  1. additionbefore pouring
  2. filtrationA fine white precipitate was filtered off

Sources & evidence

ORD record
ord-9147323b5c7a40388c27166b6d716180
Source dataset
uspto-grants-2014_04
Patent number
US08697891B2

Reaction notes

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