Potassium Iodide → 3-Benzyloxy-7-iodo-2-(3,4,5-trimethoxy-phenyl)chromen-4-one

HRID 1819534Notes

Reaction equation

HRID 1819534 reaction equation
[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([I:13])=[CH:8][CH:9]=2)[O:4][C:3]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:34](Cl)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CC(C)=O>[CH2:34]([O:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([I:13])=[CH:8][CH:9]=2)[O:4][C:3]=1[C:14]1[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 578873343-Hydroxy-7-iodo-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one

Product 1

HCID 578872943-Benzyloxy-7-iodo-2-(3,4,5-trimethoxy-phenyl)chromen-4-oneYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirring suspension of 3-hydroxy-7-iodo-2-(3,4,5-trimethoxyphenyl)-chromen-4-one (0.257 g, 0.6mmol), potassium carbonate (1.48 g, 11 mmol, 19 equ), potassium iodide (0.06 g, 0.3 mmol, 0.6 equ) and benzyl chloride (0.16 ml, 1.3 mmol, 2.3 equ) in acetone (12 ml) under nitrogen was heated to reflux for one hour. The reaction was filtered and the filtrate concentrated in vacuo to give an orange solid. This solid was recrystallised from isopropanol to give 34 (0.270 g, 88%) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for one hour
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customto give an orange solid
  6. customThis solid was recrystallised from isopropanol

Sources & evidence

ORD record
ord-d0a34b7ae8094572822d8f7dc9921116
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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