Ethylparaben → Ethyl 4-(2-pyrazinylmethoxy)benzoate

Participants

Reaction Steps

To a stirred and cooled (≤5° C.) solution of 8.3 parts of 2-pyrazinemethanol, 13.3 parts of ethyl 4-hydroxybenzoate and 20.2 parts of triphenylphosphine in 178 parts of tetrahydrofuran was added dropwise a solution of 13.93 parts of diethyl azodicarboxylate in 45 parts of tetrahydrofuran. Upon completion, the reaction mixture was stirred over weekend. After evaporation, the residue was taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was stirred in 2,2'-oxybispropane. The precipitate was filtered off and the filtrate was evaporated. The residue was crystallized from 2-propanol, yielding 7.5 parts (38.7%) of ethyl 4-(2-pyrazinylmethoxy)benzoate; mp. 76.1° C. (interm. 9).

Provenance & Evidence