Hydroquinone → Ethyl 4-(4-hydroxyphenoxy)-3-methoxy-2-pentenoate

HRID 638502Notes

Reaction equation

HRID 638502 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Br[CH:10]([CH3:20])[C:11]([O:18][CH3:19])=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>CC(C)=O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH:10]([CH3:20])[C:11]([O:18][CH3:19])=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 785HydroquinoneHCID 53787831Ethyl 4-bromo-3-methoxypent-2-enoate

Product 1

HCID 54412603Ethyl 4-(4-hydroxyphenoxy)-3-methoxy-2-pentenoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The above 3-oxo ester is reduced using NaBH4 in ethanol to yield ethyl 4-[4-(6,7-dichloro-2-quinoxalyloxy)phenoxy]-3-hydroxypentanoate. Ethyl 4-(4-hydroxyphenoxy)-3-methoxy-2-pentenoate is prepared by the reaction of hydroquinone and ethyl 4-bromo-3-methoxy-2-pentenoate in the presence of base in acetone or the like under reflux.

Workup

  1. temperaturethe like under reflux

Sources & evidence

ORD record
ord-e1f02ccdffd94ceb8c2ffdcb540d90f1
Source dataset
uspto-grants-1985_12
Patent number
US04561882

Reaction notes

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