Dowd, Paul published the artcileA general approach to substituted itaconate esters, Application In Synthesis of 31253-08-4, the publication is Synthetic Communications (1993), 23(16), 2307-22, database is CAplus.
General approaches to the synthesis of various itaconates, including 3-substituted esters, are presented. The complementary nature of the 3 methods is also shown. Thus, alkylation of Me2NCH2CH2CO2Et by treatment with LiN(CHMe2)2 (LDA), then RCHXCO2R2 (e.g., R = H, R2 = Et, X = Br) affords Me2NCH2CH(CO2R1)CHRCO2R2 (42-82% yield) which are then quaternized with MeI and treated with DBU to give the elimination products, itaconate diesters RCH(CO2R2)C(:CH2)CO2R1 (86-93% yield). Deprotonation of Me2NCH2CH(CO2R1)CH2CO2R2 (e.g., R1 = R2 = Et) with LDA and subsequent alkylation with RX (e.g., MeI) affords Me2NCH2CH(CO2R1)CHRCO2R2 in 17-46% yield. Subsequent quaternization and elimination reaction of the latter afford itaconate diesters RCH(CO2R2)C(:CH2)CO2R1 in good yield. A third alternative procedure consists of deprotonation of (EtO)2P(O)CH2CO2R1 with NaH, alkylation with RCHXCO2R2 to give (EtO)2P(O)CH(CO2R1)CHRCO2R2 (51-74% yield), and subsequent methylenation with HCHO to give the itaconate diesters in 55-93% yield.
Synthetic Communications published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Application In Synthesis of 31253-08-4.
Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com