Novel process for preparation of 1-furenyl-2,2-dimethyl-cyclopro

Details Novel process for preparation of 1-furenyl-2,2-dimethyl-cyclopro Novel process for preparation of 1-furenyl-2,2-dimethyl-cyclopro

1985-07-29

1987-02-10

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

549341, 549333, 549373, 549375, 549451, 549453, 558357, 558397, 558428, 558434, 560 11, 560118, 562429, 562500, 562506, C07C 69757

Patent

active

046423729

ABSTRACT:
A process for the preparation of cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein Z is selected from the group consisting of --CN, --COOH and --COOR.sub.1, R.sub.1 is alkyl of 1 to 6 carbon atoms and R.sub.2 and R.sub.3 are alkyl of 1 to 4 carbon atoms or taken together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms comprising reacting at low temperatures in a solvent in the presence of a strong base a compound of the formula ##STR2## wherein Z has the above definitions and R is alkyl of 1 to 6 carbon atoms or together form a polymethylene of 2 to 3 carbon atoms with a sulfone of the formula ##STR3## wherein R.sub.2 and R.sub.3 have the above definitions and Y is an aromatic group followed by aqueous treatment to obtain a compound of the formula ##STR4## wherein Y, R, R.sub.2, R.sub.3 and Z have the above definitions, reacting the latter at a low temperature in a solvent with a strong base while letting the temperature rise to obtain a compound of the formula ##STR5## wherein R, R.sub.2, R.sub.3 and Z have the above definitions of the cis/trans configuration richer in the trans isomer and either reacting the latter when Z is --CN or --COOR.sub.1 with a strong base in an aqueous media followed by acidification to obtain a compound of the formula ##STR6## wherein R, R.sub.2 and R.sub.3 have the above definitions having the same configuration as the compound of formula V or reacting the compound of formula V or Va with an acid agent in an aqueous media to obtain the corresponding compound of formula I with the same configuration as the compound of formula V or Va and optionally treating the latter with a weak base at room temperature to obtain the compound of formula I with a trans configuration which are valuable intermediates for the preparation of esters of cyclopropane carboxylic acid having elevated insecticidal activity.

REFERENCES:
patent: Re27592 (1973-03-01), Martel
patent: 3567780 (1971-03-01), Martel
patent: 3711555 (1973-01-01), Martel
Devos, Tetrahedron Letters, pp. 3911-3914 (1976).
Allinger, "Organic Chemistry", pp. 477-478, 532-537 and 585 (1971).
House, "Modern Synthetic Reactions", 2nd Ed, Benjamin Cummings Publg. Co., Menlo Park, Calif., pp. 598, 602 & 614 (1972).

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