Diethyl Oxalate → Ethyl 2,4-dioxo-4-(pyridin-4-yl)butanoate

HRID 1522476Notes

Reaction equation

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

Participants

Reactant 3

HCID 7268Diethyl Oxalate

HCID 142824-Acetylpyridine

HCID 5360545Sodium

Product 1

HCID 23005473Ethyl 2,4-dioxo-4-(pyridin-4-yl)butanoate

Procedure

The title compound was prepared in the same manner as intermediate 29 using sodium metal (0.466 g, 20.26 mmol), 1-(4-pyridinyl)ethanone (1 g, 6.66 mmol), and diethyl ethanedioate (2.388 mL, 17.62 mmol). The crude product was purified using column chromatography (0 to 100% EtOAc/hexanes) to give 0.95 g of product (24%). LCMS E-S (M+H)=222.0. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.37-1.55 (m, 3 H), 4.43 (q, J=7.07 Hz, 2 H), 7.06-7.16 (m, 1 H), 7.72-7.92 (m, 2 H), 8.82-8.94 (m, 2 H).

Workup

customThe crude product was purified

Sources & evidence

ORD record: ord-6bb14991835247a884efad5e91c8f8f4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073924B2

Reaction notes

Loading…