Process for the preparation of 3-hydroxyoxetanes

Details Process for the preparation of 3-hydroxyoxetanes Process for the preparation of 3-hydroxyoxetanes

C - Chemistry, Metallurgy

07

D

C07D 305/08 (2006.01) C07D 405/12 (2006.01) C07D 409/12 (2006.01)

Patent

CA 2180074

A process for the preparation of 3-hydroxyoxetanes of formula I (see formula I) wherein R9 and R10 are each independently of the other hydrogen or C1-C4alkyl, by (1) reaction of a carboxylic acid R-CO2H, wherein R is branched alkyl, with an epichloro-hydrin of formula II (see formula II) wherein R9 and R10 are as defined hereinbefore, to form an ester of formula III (see formula III) wherein R, R9 and R10 are as defined hereinbefore, (2) reaction of that ester with an ether of formula IV CHR1=CH-O-R2 (IV), wherein R1 is hydrogen or methyl, R2 is C1-C6alkyl, or R1 and R2 together form a radical of formula -(CH2)3-, in the presence of a catalyst, to form an ester of formula V (see formula V) (3) hydrolysis and cyclisation of that ester in the presence of a base to form a compound of formula VI (see formula VI) wherein R1, R2, R9 and R10 are as defined hereinbefore, (4) acetal cleavage in the presence of an acid to form the corresponding 3- hydroxyoxetane and (5) isolation of that 3-hydroxyoxetane.

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