2,5-SUBSTITUTED FURANS AND THEIR PRODUCTION

摘要

1466256 2,5-Substituted furans GRINDSTEDVAERKET AS 19 June 1974 [20 June 1973] 29241/73 Heading C2C Novel compounds of the formula I wherein RSP1/SP is C 1-4 alkyl or -(CH 2 ) 7 COOR in which R is hydrogen or C 1-4 alkyl; Z is either RSP4/SP is hydroxy and RSP5/SP is hydrogen or C 1-4 alkyl or RSP4/SP and RSP5/SP together are oxo and RSP6/SP is C n H 2n+1 where n is 1 to 10 with the proviso that when RSP1/SP is methyl and RSP4/SP and RSP5/SP together are oxo, Z is -CH=CH- but RSP6/SP is not methyl, may be prepared by condensing an 5-R-substituted furfural with 2-oxo(C 3-12 ) alkane or RSP6/SPCOCH 3 or RSP6/SPCOCH 2 PO(OCH 3 ) 2 to yield a compound I in which RSP4/SP and R5 together are oxo and Z is -CH=CH- optionally followed by one or more of (1) reduction of the double bond at Z, (2) reduction of the oxo group to CHOH, (3) reaction of the oxo group with a Grignard reagent RSP5/SPMgX where X is halogen to form a group, (4) hydrolysis of an ester at ROOC- and (5) esterification of a free acid at ROOC-. Pharmaceutical compositions of the compounds I with the usual excipients control hormone production of corpus luteum.