Diethyl Oxalate → Ethyl 4-(4-methoxyphenyl)-2,4-dioxobutanoate

HRID 1522472Notes

Reaction equation

[Na].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH2:11][C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1

Participants

Reactant 3

HCID 7268Diethyl Oxalate

HCID 74764'-Methoxyacetophenone

HCID 5360545Sodium

Product 1

HCID 287267Ethyl 4-(4-methoxyphenyl)-2,4-dioxobutanoate

Procedure

The title compound was prepared in the same manner as intermediate 29 using sodium metal (0.168 g, 7.32 mmol), 1-[4-(methyloxy)phenyl]ethanone (1 g, 6.66 mmol), and diethyl ethanedioate (0.903 mL, 6.66 mmol). The crude product was purified using column chromatography (0 to 100% EtOAc/hexanes) to give 0.95 g of product (57%). LCMS E-S (M+H)=250.9. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.43 (m, 3 H), 3.91 (s, 3 H), 4.41 (q, J=6.65 Hz, 2 H), 6.94-7.12 (m, 3 H), 8.01 (d, J=8.59 Hz, 2 H).

Workup

customThe crude product was purified

Sources & evidence

ORD record: ord-9eaad6623eed4f3193370fc472cc8b06
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073924B2

Reaction notes

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