Diethyl Oxalate → Ethyl 5-methoxy-2,4-dioxopentanoate

Participants

Reaction Conditions

Reaction Steps

Methoxyacetone (5.22 mL, 56.8 mmol) was added dropwise to a cold (0° C.), stirred solution of sodium ethoxide (21% in EtOH, 20.2 g, 62.4 mmol) and EtOH (50 mL), under an argon atmosphere. The reaction mixture was stirred for 30 min at 0° C. Then, diethyl oxalate (7.71 mL, 56.8 mmol) was added. The reaction mixture was allowed to warm to rt, stirred for 16 h, quenched by addition of 1N HCl (75 mL), and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and the solvent was evaporated off under reduced pressure. The crude material was purified by silica gel column chromatography (hexane/EtOAc 5-10%) to afford the title compound (3.21 g) as a yellow oil. tR: 0.70 min (LC-MS 2); ESI-MS: 189.1 [M+H]+ (LC-MS 2); Rf=0.25 (hexane/EtOAc 1:1, CPS staining).

Provenance & Evidence