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Potassium Carbonate → 4-(4-((6-Chloro-2-quinoxalinyl)oxy)phenoxy)2-penten-1-ol

HRID 466469
Notes
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Reaction equation

HRID 466469 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=2)[N:3]=1.[OH:13][C:14]1[CH:26]=[CH:25][C:17]([O:18][CH:19]([CH3:24])/[CH:20]=[CH:21]/[CH2:22][OH:23])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([O:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH:19]([CH3:24])[CH:20]=[CH:21][CH2:22][OH:23])=[CH:25][CH:26]=1)[CH:11]=[N:10]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 877482,6-DichloroquinoxalineHCID 12922586(E)-4-(4-hydroxyphenoxy)-2-penten-1-ol

Product 1

HCID 542751324-(4-((6-Chloro-2-quinoxalinyl)oxy)phenoxy)2-penten-1-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.99 g (10 mmol) of 2,6-dichloroquinoxaline, 2.13 g (11 mmol) of (E)-4-(4-hydroxyphenoxy)-2-penten-1-ol, 1.73 g (12.5 mmol) of powdered, anhydrous potassium carbonate and 50 ml of dry acetonitrile was warmed at reflux under nitrogen for a period of 3 hours. The mixture was cooled to room temperature, and the solid filtered off and washed well with ether. The filtrates were combined and evaporated to dryness, and the residue partitioned between ether and 2 percent aqueous sodium hydroxide. The aqueous layer was separated and extracted again with ether. The combined organic layers were washed with water, dried over MgSO4 and evaporated to dryness. The residual solid was purified by preparative scale HPLC, eluting with 7:3 hexane: ethyl acetate, to give a solid which was recrystallized from toluene. This gave 2.60 g (73%) of the desired pentenol as pale yellow crystals, having a melting point (m.p.) of 124°-126° C.

Workup

  1. temperatureat reflux under nitrogen for a period of 3 hours
  2. filtrationthe solid filtered off
  3. washwashed well with ether
  4. customevaporated to dryness
  5. customthe residue partitioned between ether and 2 percent aqueous sodium hydroxide
  6. customThe aqueous layer was separated
  7. extractionextracted again with ether
  8. washThe combined organic layers were washed with water
  9. dry with materialdried over MgSO4
  10. customevaporated to dryness
  11. customThe residual solid was purified by preparative scale HPLC
  12. washeluting with 7:3 hexane
  13. customethyl acetate, to give a solid which
  14. customwas recrystallized from toluene
  15. customa melting point (m.p.) of 124°-126° C.

Sources & evidence

ORD record
ord-8b8763433fa54c3cac643d5838f0fd27
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05156667

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes