Novel process

Details Novel process Novel process

1984-02-24

1987-06-02

Brust, Joseph P.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

558371, 560 17, 560 51, 560145, 560150, 560174, 560190, 560205, 568 28, 568312, 568388, 568 31, C07C 49203, C07C 69533, C07C12000, C07C12130

Patent

active

046705775

ABSTRACT:
A novel process for the preparation of pent-4-enoic acids of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, cyano and alkoxycarbonyl of 2 to 5 carbon atoms and Y is selected from the group consisting of hydrogen, cyano, alkoxycarbonyl 2 to 5 carbon atoms, acyl of an organic carboxylic acid of 2 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with the proviso that X and Y are not both hydrogen comprising reacting a compound of the formula ##STR2## wherein R is selected from the group consisting of acyloxy of an organic carboxylic acid of 1 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with an anion derivative of a compound of the formula ##STR3## wherein X.sub.1 and Y.sub.1 have the above definition for X and Y, respectively, except hydrogen in the presence of a palladium compound or nickel (o) complex and optionally a catalytic quantity of a ligand to obtain a compound of the formula ##STR4## wherein X.sub.1 and Y.sub.1 have the above definition and optionally subjecting the latter to a decarbalkoxylation when X.sub.1 or Y.sub.1 is alkoxycarbonyl or to a reduction when X.sub.1 is arylsulfonyl to obtain the corresponding compound of formula I.

REFERENCES:
patent: 4362670 (1982-12-01), Woo
Cuvigny, et al.; Journal of Organometallic Chemistry, 285, (1985), pp. 395-413.
Miller, et al.; J. Chem. Soc.--Perkin I, (1973), pp. 603-606.
Billington; Chem. Soc. Rev., 1985, 14; pp. 93-120.
Baker; Chem. and Ind., 18, Oct. 1980, pp. 816-823.
Trost, et al.; J. Org. Chem., 40, (1975), pp. 3617-3619.
Trost, et al.; J. Org. Chem.; 41, (1976), pp. 3215-3216.

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