Propargyl bromide → 7-Propynyloxy-2-methyl-4'-methoxyisoflavone

HRID 396410Notes

Reaction equation

HRID 396410 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[C:8]([CH3:12])[O:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[C:29]#[CH:30]>CC(C)=O>[C:28]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[C:8]([CH3:12])[O:9]2)=[CH:4][CH:3]=1)#[C:29][CH3:30]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 54002317-hydroxy-3-(4-methoxyphenyl)-2-methyl-4H-chromen-4-one

Product 1

HCID 181718487-Propynyloxy-2-methyl-4'-methoxyisoflavone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-hydroxy-2-methyl-4′-methoxyisoflavone (2.82 g, 0.01 mol), K2CO3 (2.8 g, 0.02 mol), Kl (0.166 g, 0.001 mol), propargyl bromide (1.78 g, 0.015 mol) and acetone (100 mL) was refluxed 10 h and hot filtered. The solvent was evaporated and the residue was crystallized by toluene. This yields 2.24 g of a product with the following characteristics: m.p. 139-140° C.; 1H NMR (CDCl3) δ: 2.29 (s, 3H), 2.6 (m, 1H), 3.85 (s, 3H), 4.75 (s, 2H), 6.93-8.17 (m, 7H).

Workup

  1. temperaturewas refluxed 10 h
  2. customThe solvent was evaporated
  3. customthe residue was crystallized by toluene

Sources & evidence

ORD record
ord-56b485669caf4cdc8491735f11cb1a87
Source dataset
uspto-grants-2003_08
Patent number
US06608089B2

Reaction notes

Loading…