2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER synthesis
- Product Name:2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER
- CAS Number:34034-87-2
- Molecular formula:C8H11ClO5
- Molecular Weight:222.62
Yield: 71%
Reaction Conditions:
with sodium t-butanolate in tetrahydrofuran at 0;
Steps:
15 5.15. Diethyl 2-chloro-3-oxosuccinate (18)
NaOtBu (96.1 g, 1.0 mol) was dissolved in THF (1 L), and the solution was cooled to 0 °C. At this temperature with vigorous mechanical stirring, a mixture of ethyl chloroacetate (107 mL, 1.0 mol) and diethyl oxalate (136 mL, 1.0 mol) was added dropwise. The mixture was left overnight, and aqueous HCl (90 mL + 400 mL H2O) was added. The resulted solution was extracted with CH2Cl2 (3 * 200 mL). The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was distilled at reduced pressure (bp = 110-140 °C, 10 torr). M = 157.6 g. Yield = 71%. 1H NMR: (CDCl3, 400 MHz) δ = 1.31 (t, J = 7.2 Hz, 3 H), 1.39 (t, J = 7.2 Hz, 3 H), 4.31 (q, J = 7.2 Hz, 2 H), 4.39 (q, J = 7.2 Hz, 2 H), 5.46 (s, 1 H).
References:
Curreli, Francesca;Belov, Dmitry S.;Kwon, Young Do;Ramesh, Ranjith;Furimsky, Anna M.;O'Loughlin, Kathleen;Byrge, Patricia C.;Iyer, Lalitha V.;Mirsalis, Jon C.;Kurkin, Alexander V.;Altieri, Andrea;Debnath, Asim K. [European Journal of Medicinal Chemistry,2018,vol. 154,p. 367 - 391]
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1000210-73-0
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34034-87-2
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