Potassium Carbonate → Ethyl 4-[4-(6,7-dichloro-2-quinoxalyloxy)phenoxy]-3-methoxy-2-pentenoate

HRID 638501Notes

Reaction equation

HRID 638501 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:13])=[C:7]([Cl:12])[CH:8]=2)[N:3]=1.[OH:14][C:15]1[CH:32]=[CH:31][C:18]([O:19][CH:20]([CH3:30])[C:21]([O:28][CH3:29])=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[Cl:13])[N:3]=[C:2]([O:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH:20]([CH3:30])[C:21]([O:28][CH3:29])=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:31][CH:32]=1)[CH:11]=[N:10]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 100369782,6,7-TrichloroquinoxalineHCID 54412603Ethyl 4-(4-hydroxyphenoxy)-3-methoxy-2-pentenoate

Product 1

HCID 54001181Ethyl 4-[4-(6,7-dichloro-2-quinoxalyloxy)phenoxy]-3-methoxy-2-pentenoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,6,7-trichloroquinoxaline (0.8 eq, 3.43 ml.), ethyl 4-(4-hydroxyphenoxy)-3-methoxy-2-pentenoate (1.09 g, 1.2 eq), K2CO3 (568 mg) and CH3CN (20 ml) is refluxed overnight and then filtered. The filtrate is concentrated and taken up in CH2Cl2. The CH2Cl2 solution is washed, dried and evaporated to dryness to yield crystalline enol ether, i.e., ethyl 4-[4-(6,7-dichloro-2-quinoxalyloxy)phenoxy]-3-methoxy-2-pentenoate.

Workup

  1. temperatureis refluxed overnight
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated
  4. washThe CH2Cl2 solution is washed
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e987836e973e4866a2cb6229ae71811e
Source dataset
uspto-grants-1985_12
Patent number
US04561882

Reaction notes

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