Diethyl Oxalate → Ethyl 3-[2-(2-methoxyethoxy)-5-nitropyridin-4-yl]-2-oxopropionate potassium salt

HRID 2250438Notes

Reaction equation

[K:1].[CH3:2][O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][N:8]=1.[CH2:17]([O:19][C:20](=[O:26])[C:21](OCC)=[O:22])[CH3:18]>C(OCC)C.C(O)C.C1(C)C=CC=CC=1>[K:1].[CH2:17]([O:19][C:20](=[O:26])[C:21](=[O:22])[CH2:13][C:11]1[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][N:8]=[C:7]([O:6][CH2:5][CH2:4][O:3][CH3:2])[CH:12]=1)[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To 265 mg (6.78 mmol) potassium in 20 mL absolute diethylether, 2.5 mL ethanol were slowly added. The mixture is cooled to 0° C. and a solution of 720 mg (3.39 mmol) 2-(2-Methoxy-ethoxy)-4-methyl-5-nitro-pyridine in 2.5 mL of absolute diethylether and 0.5 mL ethanol were added. 3.966 g (27.14 mmol) oxalic acid diethylester in 15 mL toluene were added tropwise over 45 min. The reaction mixture was stirred at room temperature for 4 h. The precipitate was filtered, washed with diethyl ether/n-heptane 1/1 and dried in vacuo. 1.4 g of 3-[2-(2-Methoxy-ethoxy)-5-nitro-pyridin-4-yl]-2-oxo-propionic acid ethylester potassium salt were isolated as a red solid and used in the next step without further purification.

Workup

filtrationThe precipitate was filtered
washwashed with diethyl ether/n-heptane 1/1
customdried in vacuo

Sources & evidence

ORD record: ord-3bf07c71ef3e41e0a220ba4cfca77219
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317027B2

Reaction notes

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