ChemicalBook CAS DataBase List ethyl 4-methyl-2-oxovalerate

ethyl 4-methyl-2-oxovalerate synthesis

7synthesis methods

Product Name:ethyl 4-methyl-2-oxovalerate
CAS Number:26073-09-6
Molecular formula:C8H14O3
Molecular Weight:158.2

926-62-5 Synthesis

926-62-5
163 suppliers
$154.00/250g

95-92-1 Synthesis

95-92-1
408 suppliers
$5.00/5G

26073-09-6
43 suppliers
$220.00/250mg

Yield:26073-09-6 76%

Reaction Conditions:

in diethyl ether at -78 - 20; for 2 h;Inert atmosphere;

Steps:

Synthesis of ethyl 4-methyl-2-oxopentanoate (4)

730 mg (5 mmol) of diethyl oxalate and 12 mL of anh. diethyl ether were introduced into a 100 mL round-bottom flask under argon atmosphere. The resulting solution was cooled to -78 °C and a solution of the Grignard reagent described above (compound 3, 1.5 eq.) was added. The reaction mixture was stirred at rt for 2 h, after which time the reaction was quenched with NH4Cl 1M and extracted three times with Et2O. The combined organic phases were dried over anh. Na2SO4 and the volatile compounds in the filtrate were removed under reduced pressure. The crude reaction product was purified by column chromatography, yielding 601 mg of compound 4 as a colorless oil in 76% yield. ¹H NMR (300 MHz, CDCl3) δ (ppm): 4.28 (q, J=7.2 Hz, 2H, CH2, Et), 2.68 (d, J=6.6 Hz, 2H,CH2iBu), 2.16 (sept, J=6.9 Hz, 1H, CHiBu), 1.33 (t, J=7.2 Hz, 3H, CH3, Et), 0.93 (d, J=6.9 Hz, 6H,2 x CH3iBu); ¹³C NMR (75 MHz, CDCl3) δ (ppm): 194.5 (C2), 161.5 (C1), 62.4 (CH2, Et), 48.0 (C3, CH2iBu), 24.3 (C4, CHiBu), 22.5 (2 x CH3iBu), 14.1 (CH3, Et); HRMS (ESI): Calcd. for C8H14O3: 158.0943; found: 158.0951.

References:

Bueno, José María;Carda, Miguel;Crespo, Benigno;Cu?at, Ana Carmen;de Cozar, Cristina;León, María Luisa;Marco, J. Alberto;Roda, Nuria;Sanz-Cervera, Juan F. [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 16,p. 3938 - 3944] Location in patent:supporting information