A General Approach to Substituted Itaconate Esters

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• Obtained in 44% yield, after flash chromatography on silica gel with 3:2 v/v hexane/ethyl acetate, as a 1.7:1 mixture (by GC-MS) of the diastereoisomers. Rf = 0.06 (10% ethyl acetate in hexane); for comparison Rf value of the starting ester was 0.34. One of the isomers (tr= 2.23 in GC-MS) was isolated in a pure form. 1H-NMR 4.24–4.11 (m, 2H), 3.83 (s, 1H), 2.70–2.61 (m, 1H), 2.56–2.48 (m, 1H), 2.10–1.92 (m, 2H), 1.46 (s, 9H), 1.43 (s, 3H), 1.25 (t, J=7.0, 3H). 13C-NMR 210.1 (s), 171.0 (s), 170.1 (s), 84.2 (s), 80.3 (s), 61.7 (t, J=151), 55.4 (s), 31.8 (t, J=135), 31.7 (t, J=135), 27.8 (q, J=127), 21.7 (q, J=131), 14.2 (q, J=128). IR 3468 (s br, OH), 2982, 2938, 1753, 1734 (br), 1458, 1395, 1372, 1304, 1275, 1155, 1107, 1024. MS (tr=2.23) 230 (30, M+-Me2=CH2), 202 (17, M+-Me2=CH2 -C2H4), 184 (30, M+-HCOOtBu), 185 (39, M+-COOtBu), 156 (34, M+-Me2=CH2 -HCOOEt), 139 (14, M+-COOtBuEtOH), 57 (100, Me3C+). MS of the other isomer (tr =2.39) 257 (5, M+-Et), 230 (30, M+-Me2=CH2), 202 (16, M+-Me2=CH2 -C2H4), 184 (28, M+-HCOOtBu), 185 (18, M+-COOtBu), 156 (19, M+-Me2=CH2 -HCOOEt), 139 (14, M+-COOtBu-EtOH), 57 (100, Me3C+). HRMS of the mixture of both isomers as calc'd for C10H14O6: 230.0790; found 230.0776.
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• Diethyl itaconate was prepared according to ref 1c.
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