Diethyl Malonate → Diethyl-2-[4'-(4"-cyano-phenoxy)-phenoxy]-propionyl-malonate

HRID 35145Notes

Reaction equation

HRID 35145 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[C:22]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].[Mg].C(OCC)(=O)CC(OCC)=O>CCOCC>[CH2:27]([O:26][C:24](=[O:25])[CH:23]([C:14](=[O:15])[CH:13]([O:12][C:11]1[CH:18]=[CH:19][C:8]([O:7][C:6]2[CH:20]=[CH:21][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1)[CH3:17])[C:22]([O:30][CH2:31][CH3:32])=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 133627952-[4'-(4"-Cyano-phenoxy)-phenoxy]-propionyl chlorideHCID 86615207Magnesium diethyl malonate

Product 1

HCID 21295006Diethyl-2-[4'-(4"-cyano-phenoxy)-phenoxy]-propionyl-malonateYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 30 g of 2-[-4'-(4"-cyano-phenoxy)-phenoxy]-propionyl chloride and 30 ml of ether is added dropwise to a 35% etheral solution of magnesium diethyl malonate prepared from 17.6 g of diethyl malonate. The addition of the acid chloride having been completed the reaction mixture is heated to boiling for an hour and worked up as described in Example 1. Thus 30 g of the desired compound are obtained in the form of a viscous oil which solidifies on standing and melts at 42°-46° C. Yield 72%.

Workup

  1. temperatureis heated
  2. waitto boiling for an hour

Sources & evidence

ORD record
ord-234774c10a5b45eabb39c4341e40c26c
Source dataset
uspto-grants-1988_08
Patent number
US04765825

Reaction notes

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