ChemicalBook CAS DataBase List 2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER

2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER synthesis

6synthesis methods

Product Name:2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER
CAS Number:34034-87-2
Molecular formula:C8H11ClO5
Molecular Weight:222.62

105-39-5 Synthesis

105-39-5
405 suppliers
$10.00/5g

95-92-1 Synthesis

95-92-1
420 suppliers
$5.00/5 g

2-CHLORO-3-OXO-SUCCINIC ACID DIETHYL ESTER

34034-87-2
150 suppliers
$8.00/1g

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]

141-78-6 Synthesis