Carbon-11 labeled acetone is a useful radiosynthetic precursor. Previously, strict control of no-carrier-added stoichiometry was required to prepare it from reaction of CO2 and methyl lithium. However, excess methyl lithium may be selectively quenched to avoid reaction with nascent acetone to give tert-butanol. We report a simple pKa-based strategy to sequentially and selectively quench MeLi and acetone to give yields of up to 100% acetone even in the presence of a large excess of MeLi. The method gives good yields of acetone under conditions that previously precluded its synthesis
Studenov, A., Berridge, M., Soloviev, D., Matarrese, M., Todde, S. (1999). High yield synthesis of [11C]-acetone through selective quenching of methyl lithium. NUCLEAR MEDICINE AND BIOLOGY, 26(4), 431-435 [10.1016/S0969-8051(99)00003-7].
High yield synthesis of [11C]-acetone through selective quenching of methyl lithium
TODDE, SERGIO CAMILLO
1999
Abstract
Carbon-11 labeled acetone is a useful radiosynthetic precursor. Previously, strict control of no-carrier-added stoichiometry was required to prepare it from reaction of CO2 and methyl lithium. However, excess methyl lithium may be selectively quenched to avoid reaction with nascent acetone to give tert-butanol. We report a simple pKa-based strategy to sequentially and selectively quench MeLi and acetone to give yields of up to 100% acetone even in the presence of a large excess of MeLi. The method gives good yields of acetone under conditions that previously precluded its synthesis
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