Natural Science Forum / Chemistry / Organic Synthesis / April 2005

hi,

in literature i found quite interesting procedure for reducing
carboxylic acids without touching ester moiety. in typical procedure
the suspension of sodium borohydride in thf is treated with acid. then
the solution of iodine in thf is added dropwise. some authors observed
the traces of iodobutanol (thf cleavage product). unfortunately, i
always obtain ONLY iodobutanol without any traces of desired product.

my substrate to be reduced is 5-oxotetrahydrofuran-2-carboxylic acid.
probably lactone ring is too labile under such conditions.

does anybody have experience with this reduction protocol? any
suggestion what went wrong? can you recommend me another reagent for
such reaction (except of borane-dimethylsulfide comlex)

thanks in advance