Imidazole → HCID 57890279, compound

HRID 2367650Notes

Reaction equation

HRID 2367650 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([CH3:23])[C:13]([O:19]C(=O)C)=[CH:14][CH:15]=3)[O:10][CH2:9]2)=[CH:4][CH:3]=1.N1C=CN=C1>CCO>[OH:19][C:13]1[C:12]([CH3:23])=[C:11]2[C:16]([C:17](=[O:18])[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)[CH2:9][O:10]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 66657087HCID 66657087, compound

Product 1

HCID 57890279HCID 57890279, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetic acid 3-(4-hydroxy-phenyl)-8-methyl-4-oxo-chroman-7-yl ester (18.37 g), imidazole (21.18 g, 6 equivalents) and 100% EtOH (536 ml) were added to a round bottom flask (2 L). The reaction mixture was refluxed and monitored by HPLC. The reaction was completed at 8 hours. The reaction mixture was reduced (˜130 ml) on a rotary evaporator and poured into stirred, chilled distilled water (1.9 L). The water crash out was left stirring in the cold room overnight. The pale pink solid was collected by suction filtration. NMR of the solid indicated it was 7-Hydroxy-3-(4-hydroxy-phenyl)-8-methyl-chroman-4-one with >95% purity. The solid was dried on the freeze dryer for 3 hours (8.31 g, 59%).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. customon a rotary evaporator
  3. additionpoured
  4. temperaturechilled
  5. distillationdistilled water (1.9 L)
  6. waitThe water crash out was left
  7. stirringstirring in the cold room overnight
  8. filtrationThe pale pink solid was collected by suction filtration
  9. customThe solid was dried on the freeze dryer for 3 hours (8.31 g, 59%)

Sources & evidence

ORD record
ord-61cde52a49194a229861e01fd17604ad
Source dataset
uspto-grants-2014_04
Patent number
US08697891B2

Reaction notes

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