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

HRID 1199296Notes

Reaction equation

HRID 1199296 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:12])[CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:19][C:20]1[CH:32]=[CH:31][C:23]([O:24][CH:25]([CH3:30])[CH:26]=[CH:27][CH2:28][OH:29])=[CH:22][CH:21]=1>CS(C)=O>[F:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([O:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH:25]([CH3:30])[CH:26]=[CH:27][CH2:28][OH:29])=[CH:31][CH:32]=1)[CH:11]=[N:10]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 126864072-Chloro-6-fluoroquinoxalineHCID 541420004-(4-Hydroxyphenoxy)-2-penten-1-ol

Product 1

HCID 540980444-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-2-penten-1-olYield 44.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1.28 g (7 mmol) of 2-chloro-6fluoroquinoxaline, 1.16 g (8.4 mmol) of anhydrous, powdered potassium carbonate, 1.55 g (8 mmol) of 4-(4-hydroxyphenoxy)-2-penten-1-ol and 20 ml of DMSO was warmed, under nitrogen, at 110° C. for a period of 2 hours. The mixture was cooled to room temperature, poured into dilute, aqueous HCl and extracted with two portions of ether. The combined organic layers were washed twice with 1 percent aqueous NaOH and with water, dried over MgSO4 and evaporated to dryness. The residue was purified by preparative scale HPLC, eluting with 3:1 hexane:acetone. After removal of solvent the resulting tan crystals were recrystallized from methylcyclohexane to give 1.05 g of crystals which were further purified by recrystallization from toluene to leave nearly colorless crystals, m.p. 109-111° C. (Compound F)

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. additionpoured
  3. additioninto dilute
  4. extractionaqueous HCl and extracted with two portions of ether
  5. washThe combined organic layers were washed twice with 1 percent aqueous NaOH and with water
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe residue was purified by preparative scale HPLC
  9. washeluting with 3:1 hexane
  10. customAfter removal of solvent the resulting tan crystals
  11. customwere recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-9515b42bd4e14234aa833345f048c009
Source dataset
uspto-grants-1990_02
Patent number
US04900354

Reaction notes

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