Potassium Carbonate → HCID 19913832, compound

HRID 1090795Notes

Reaction equation

HRID 1090795 reaction equation
Cl[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.[C:21]([C:26]1[O:27][C:28]2[C:33]([C:34](=[O:44])[C:35]=1[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[C:32]([OH:45])[CH:31]=[C:30]([OH:46])[CH:29]=2)([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:21]([C:26]1[O:27][C:28]2[CH:29]=[C:30]([O:46][CH2:2][C:3]3[CH:20]=[CH:19][C:6]([O:7][CH2:8][C:9]4[CH:18]=[CH:17][C:16]5[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=5)[N:10]=4)=[CH:5][CH:4]=3)[CH:31]=[C:32]([OH:45])[C:33]=2[C:34](=[O:44])[C:35]=1[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53801872-Carbethoxy-5,7-dihydroxy-4'-methoxyisoflavoneHCID 147741632-(4-Chloromethylphenoxy)methylquinoline

Product 1

HCID 19913832HCID 19913832, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.62 g of 2-(4-chloromethylphenoxy)methyl quinoline, 0.78 g of 2-carboethoxy-5,7-dihydroxy-4'-methoxy isoflavone and 0.31 g potassium carbonate are refluxed in 30 ml of acetone for 17 hours. The mixture was concentrated and the crude product purified by flash chromatography on silica gel and crystallized from toluene to give 2-carboethoxy-5-hydroxy-3-(4-methoxyphenyl)-7-(4-(quinolin-2- ylmethoxy)benzyloxy)-4-oxo-4H-1-benzopyran.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude product purified by flash chromatography on silica gel
  3. customcrystallized from toluene

Sources & evidence

ORD record
ord-6a41f468fcf344dfa0b36018d73ab6b9
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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