Imidazole → HCID 57890276, compound

HRID 2280229Notes

Reaction equation

HRID 2280229 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-c5004a6432914d9bb5692a0c84335982
Source dataset
uspto-grants-2015_09
Patent number
US09138478B2

Reaction notes

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