Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1995-10-03
1998-04-28
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 60, 560 9, 546 341, C07C 6973
Patent
active
057446350
DESCRIPTION:
BRIEF SUMMARY
This is the U.S. National Stage Application of PCT/FR94/00418 filed Apr. 14, 1994 now WO94/24085 published Oct. 27, 1994.
The present invention relates to a preparation process for derivatives of beta-alkoxy acrylic acid.
A subject of the invention is a preparation process for compounds of formula (I): ##STR2## in which R represents an optionally substituted alkenyl or alkynyl radical containing up to 8 carbon atoms, an optionally substituted monocyclic or polycyclic aryl or heteroaryl radical, R.sub.1 and R.sub.2, identical or different, represent an alkyl radical containing up to 4 carbon atoms, characterized in that a compound of formula (II): ##STR3## in which X represents a halogen atom, is subjected to the action of an organometallic compound of formula (III): metallic derivative, or a compound of formula (II'): ##STR4## in which Z' represents a metal or a metallic derivative and R.sub.1 and R.sub.2 have the definition indicated previously, is subjected to the action of a compound of formula (III'): reaction leaving group, in order to obtain the corresponding compound of formula (I).
By alkyl radical represented by R.sub.1 and R.sub.2 is meant a methyl, ethyl, linear or branched propyl, linear or branched butyl radical.
When R represents an alkenyl radical, it is preferably a vinyl, allyl, butenyl, pentenyl, hexenyl, or cyclohexenyl radical.
When R represents an alkynyl radical, it is preferably an ethynyl, propargyl or butynyl radical.
When R represents an aryl radical, it is preferably the phenyl or naphthyl radical.
When the alkenyl or alkynyl radical is substituted, it is for example an alkoxylated substituent such as methoxy, ethoxy, propyloxy.
When R represents a heterocyclic aryl radical, it is preferably a heterocyclic radical with 5 members such as one of the following radicals: thienyl, furyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, thiadiazolyl, thiazolidinyl, dioxolannyl, pyrazolyl, oxazolyl or isoxazolyl, or also a heterocyclic radical with 6 members, such as the pyridyl, pyrimidinyl, pyridazinyl or pyrazinyl radical, or also a condensed aryl radical such as the indolyl, benzofuryl, benzothienyl, benzothiazolyl, quinolinyl, quinazolinyl or dihydroquinazolinyl radical.
When R is a a substituted aryl or heteroaryl radical, it is preferably substituted by one or more radicals chosen from the group constituted by free, salified, esterified or amidified carboxy radicals, hydroxyl radicals, halogen atoms, NH.sub.2, NO.sub.2, C.tbd.N, alkyl, alkenyl, alkynyl, aryl and heteroaryl radicals, O-alkyl, O-alkenyl, O-alkynyl, O-aryl and O-heteroaryl radicals, S-alkyl, S-alkenyl, S-alkynyl, S-aryl and S-heteroaryl radicals and N-alkyl, N-alkenyl, N-alkynyl, N-aryl and N-heteroaryl radicals containing up to 24 carbon atoms, optionally substituted by one or more halogen atoms, the radical ##STR5## and the radical --S(O).sub.t --R.sub.5, R.sub.3 and R.sub.4, identical or different, and R.sub.5 representing a hydrogen atom or an alkyl or aryl radical containing up to 12 carbon atoms, optionally substituted, and t representing the number 0, 1 or 2.
By halogen atom is meant for example a fluorine, chlorine, bromine or iodine atom.
By alkyl, alkenyl, alkynyl, aryl or heteroaryl radical which can be represented by the substituents of the aryl or heteroaryl radical or be contained in these substituents, is preferably meant one of those indicated above for R.sub.1, R.sub.2 or R.
By esterified carboxy radical is meant for example methoxycarbonyl or ethoxycarbonyl.
By salified carboxy radical is meant for example a radical salified by a sodium or potassium atom.
X represents a fluorine, chlorine, bromine or iodine atom.
When Z represents a metal, it is an alkali metal such as lithium, sodium or potassium.
When Z represents a metallic derivative, it is a derivative of an alkaline-earth metal or of a metal with a higher valency such as magnesium, calcium, titanium, nickel, copper, zinc, aluminium, boron, tin, palladium or platinum.
By derivative is meant a hydroxylated, alkoxylated, alkylated derivative or a hali
REFERENCES:
Chemical Abstracts Service Registry Handbook. Number Section. 1985 Supplement. ACS, Columbus, Ohio. RN=99503-30-7, RN=99503-34-1, 1985.
Synthetic Communications, 11(7), pp. 513-518, (1981) The Palladium-Catalyzed Cross-Coupled Reaction . . . of Bases, N. Miyaura, et al, Japan J.C.S. Chem, Comm., (1979).
Stereoselective Synthesis of Arylated . . . Palladium Catalyst, N. Miyaura, et al, pp. 866-867, (Japan).
Brayer Jean-Louis
Hodgson David Michael
Richards Ian Christopher
Witherington Jason
Geist Gary
Padmanabhan Sreeni
Uclaf Roussel
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