Potassium Carbonate → HCID 14626325, compound

HRID 478088Notes

Reaction equation

HRID 478088 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9]2)=[CH:4][CH:3]=1.Br[CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:24]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9]2)=[CH:4][CH:3]=1)[CH2:23][CH2:22][CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 707041-Pentene, 5-bromo-HCID 52818947-Hydroxyflavone

Product 1

HCID 14626325HCID 14626325, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A yellow suspension of 7-hydroxyflavone (25.66 g, 0.108 mol), 5-bromo-1-pentene (17.88 g, 14.2 ml, 0.12 mol), and anhydrous, powdered potassium carbonate (30.40 g, 0.22 mol) in acetone (500 ml) was stirred and heated at reflux for 24 hours. The tlc (thin layer chromatography), on silica gel eluted with 20% of hexane in ether, indicated that the reaction was incomplete. Additional 1.5 ml of 5-bromo-1-pentene was added and refluxing was continued for 6 hours and cooled. The solid was filtered and the filtrate was evaporated under vacuum to give a yellow solid 32.63 g, 97% yield. Recrystallization from isopropyl alcohol gave white crystals, mp 104.5°-106° C.; 55% yield (pure).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. washThe tlc (thin layer chromatography), on silica gel eluted with 20% of hexane in ether
  4. additionAdditional 1.5 ml of 5-bromo-1-pentene was added
  5. temperaturerefluxing
  6. temperaturecooled
  7. filtrationThe solid was filtered
  8. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-fd8a3ebe18604ef2a418e3aef0307a05
Source dataset
uspto-grants-1989_12
Patent number
US04889941

Reaction notes

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