Simple preparation of alpha-diazo esters.
[reaction: see text] The TiCl4-mediated reaction of an ester with benzoyl chloride results in high yields of the alpha-benzoylated ester. Diazo transfer of the benzoylated ester utilizing p-acetoamidobenzenesulfonyl azide affords the alpha-diazo ester in good yield. Using this simplified procedure, it is easy to prepare gram quantities of alpha-diazo esters.
Taber
Douglass F
DF
Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Sheth
Ritesh B
RB
Joshi
Pramod V
PV