Diethyl Malonate → Diethyl-4-[4'-(4""-trifluoromethyl-phenoxy)-phenoxy]-2-pentenoyl-malonate

HRID 1709104Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH:13]([CH3:19])[CH:14]=[CH:15][C:16](O)=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C(Cl)(=O)C(C)(C)C.C([O-])(=O)CC([O-])=O.C(C(CC)(O[Mg+2])C)C.[C:48]([O:56][CH2:57][CH3:58])(=[O:55])[CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51]>>[CH2:57]([O:56][C:48](=[O:55])[CH:49]([C:16](=[O:17])[CH:15]=[CH:14][CH:13]([O:12][C:11]1[CH:10]=[CH:9][C:8]([O:7][C:6]2[CH:22]=[CH:23][C:3]([C:2]([F:24])([F:25])[F:1])=[CH:4][CH:5]=2)=[CH:21][CH:20]=1)[CH3:19])[C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH3:58]

Participants

Reactant 3

HCID 7761Diethyl Malonate

HCID 62493Pivaloyl chloride

HCID 1577944-[4-(4-Trifluoromethylphenoxy)phenoxy]-2-pentenoic acid

Product 1

HCID 57188560Diethyl-4-[4'-(4""-trifluoromethyl-phenoxy)-phenoxy]-2-pentenoyl-malonateYield 87%

Procedure

One proceeds in an analogous manner to the process disclosed in Example 4 by reacting 4-[4'-(4"-trifluoromethyl-phenoxy)-phenoxy]-2-pentenoic acid at first with 12 g of pivaloyl chloride and thereafter with diethyl-ethoxy-magnesium malonate prepared from 17.6 g of diethyl malonate. The reaction mixture is worked up. 43 g of of the viscous oily desired compound are obtained which turns to a faint yellow crystalline product on standing. Mp.: 52°-55° C., yield 87%.

Sources & evidence

ORD record: ord-bed5ff7c26104287baba3221fc0d0979
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948420

Reaction notes

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