Acetone → HCID 18171840, compound

HRID 396412Notes

Reaction equation

HRID 396412 reaction equation
O[C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[CH:6][O:7]2.C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[C:29]#[CH:30].[CH3:32][C:33](C)=O>>[C:30]([O:12][C:10]1[CH:9]=[C:8]2[C:3]([C:4](=[O:21])[C:5]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]#[C:32][CH3:33])=[CH:15][CH:14]=3)=[CH:6][O:7]2)=[CH:2][CH:11]=1)#[C:29][CH3:28]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 5280373Biochanin A

Product 1

HCID 18171840HCID 18171840, compound

Procedure

A mixture of 5,7-dihydroxy-4′-methoxyisoflavone (2.54 g, 0.01 mol), K2CO3 (2.8 g, 0.02 mol), Kl (0.166 g, 0.001 mol), propargyl bromide (1.72 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 2.31 g of a product with the following characteristics: m.p. 162-163° C.; 1H NMR (CDCl3) δ: 2.44 (m, 1H, CH), 2.57 (m, 1H), 4.54 (s, 2H), 4.56 (s, 2H), 6.85-8.08 (m, 8H).

Workup

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

Sources & evidence

ORD record
ord-f3f46227041649038f23d9656c989f27
Source dataset
uspto-grants-2003_08
Patent number
US06608089B2

Reaction notes

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