Potassium Carbonate → Quizalofop-tefuryl

HRID 892694Notes

Reaction equation

HRID 892694 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:16]=[N:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([Cl:17])[CH:13]=3)[N:8]=2)=[CH:4][CH:3]=1.Br[CH:21]([CH3:31])[C:22]([O:24][CH2:25][CH:26]1[CH2:30][CH2:29][CH2:28][O:27]1)=[O:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:6][C:5]1[CH:18]=[CH:19][C:2]([O:1][CH:21]([CH3:31])[C:22]([O:24][CH2:25][CH:26]3[CH2:30][CH2:29][CH2:28][O:27]3)=[O:23])=[CH:3][CH:4]=1)[CH:16]=[N:15]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 109894084-[(6-Chloroquinoxalin-2-yl)oxy]phenolHCID 23286429HCID 23286429, compound

Product 1

HCID 86175Quizalofop-tefurylYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 500 milliliter roundbottom flask were added 0.055 mole of 2-(4-hydroxyphenoxy)-6-chloroquinoxaline, 0.055 mole of 2-tetrahydrofuranylmethyl 2-bromopropanoate, 0.110 mole of anhydrous potassium carbonate, and 250 milliliters of acetonitrile. The mixture was refluxed for 5.5 hours and the solvent removed. The residue was filtered through a column of alumina with dichloromethane. Solvent removal and recrystallization from boiling hexane resulted in an 85% yield of 2-tetrahydrofuranylmethyl 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propanoate. The material melted over a range of 52°-55° C.

Workup

  1. temperatureThe mixture was refluxed for 5.5 hours
  2. customthe solvent removed
  3. filtrationThe residue was filtered through a column of alumina with dichloromethane
  4. customSolvent removal and recrystallization

Sources & evidence

ORD record
ord-67548e6f6b804167a3e7f3c7035d4094
Source dataset
uspto-grants-1992_06
Patent number
US05120348

Reaction notes

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