Tetrahydrofuran → (4-(1H-Imidazol-1-yl)phenyl)methanol

Participants

Reaction Steps

To 90 parts of tetrahydrofuran were added 5 parts of lithium aluminum hydride. Then there was added dropwise (slowly) a solution of 35 parts of ethyl 4(1H-imidazol-1-yl)benzoate in 135 parts of tetrahydrofuran: temperature rose to 60° C. Upon completion, stirring was continued first for 1 hour at 60-65° C. and further overnight at room temperature. While cooling, the reaction mixture was decomposed by the successive dropwise additions of 3 parts of water, 10 parts of a sodium hydroxide solution 50% and 10 parts of water. After stirring for a while at room temperature, the precipitate was filtered off and washed with benzene. The filtrate was dried, filtered and evaporated. The residue was crystallized from 4-methyl-2-pentanone. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 16.2 parts (58%) of 4-(1H-imidazol-1-yl)-benzenemethanol; mp. 124.7° C. (intermediate 19).

Provenance & Evidence