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

Temperature

0 °C

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).

1. temperatureto warm to rt
2. stirringstirred for 16 h
3. customquenched by addition of 1N HCl (75 mL)
4. extractionextracted with CH2Cl2
5. dry with materialThe combined organic layers were dried over Na2SO4
6. customthe solvent was evaporated off under reduced pressure
7. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 5-10%)

ORD record

ord-cd1c5b248d6a4535b7aa95f2f8794c64

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975417B2