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

95-92-1

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

34034-87-2

NaOtBu (96.1 g, 1.0 mol) was dissolved in THF (1 L) and the solution was cooled to 0°C. A mixture of ethyl chloroacetate (107 mL, 1.0 mol) and diethyl oxalate (136 mL, 1.0 mol) was added slowly and dropwise at this temperature under vigorous mechanical stirring. After the reaction mixture was stirred overnight at room temperature, an aqueous HCl solution (90 mL of concentrated hydrochloric acid mixed with 400 mL of water) was added. The resulting solution was extracted with CH2Cl2 (3 x 200 mL). The organic layers were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reduced pressure distillation (boiling point range 110-140°C, pressure 10 torr). The product diethyl 2-chloro-3-oxosuccinate was obtained 157.6 g in 71% yield.1H NMR (CDCl3, 400 MHz) δ= 1.31 (t, J = 7.2Hz, 3H), 1.39 (t, J = 7.2Hz, 3H), 4.31 (q, J = 7.2Hz, 2H), 4.39 (q, J = 7.2Hz, 2H), 4.39 (q, J = 7.2Hz, 2H) 5.46 (s, 1H).

105-39-5 Synthesis

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

95-92-1 Synthesis

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

34034-87-2
146 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