4-Toluenesulfonyl chloride → p-Toluenesulfonic acid

Participants

Reaction Steps

For example, alcohol 4 was prepared with a 50-65 percent yield by coupling 2,3,-isopropylidene-D-erythrose with the known Wittig reagent (4-carbethoxybutyl) triphenylphosphonium bromide and KN(SiMe3)2 in THF at -78 degrees C. to 0 degrees C. The alcohol 4 was then treated with p-toluenesulfonyl chloride to furnish the corresponding p-toluenesulfonate. This p-toluenesulfonate was treated with sodium azide NaN3 in dimethyl formamide (DMF) (CH3)2NCHO at about 70 degrees C. to 100 degrees C. to produce the imino ester 6 having the structure ##STR11## wherein R is (C1 -C8) alkyl;

Provenance & Evidence