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

HRID 553566Notes

Reaction equation

[K:1].CCO.[CH3:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][N:11]=1.[C:20](OCC)(=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(OCC)C.C1(C)C=CC=CC=1>[K:1].[CH3:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH2:16][C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.86 g of potassium are initially charged in 120 ml of dry diethyl ether, and 15 ml of EtOH are added slowly. The mixture is cooled to 0° C. 5 g of 2-(2-methoxyethoxy)-4-methyl-5-nitropyridine are dissolved in 15 ml of dry ether and 3 ml of EtOH and added. 27.5 g of diethyl oxalate were dissolved in 100 ml of toluene and, at 0° C., added dropwise over a period of 45 min. The mixture is stirred at room temperature for 24 h. The precipitate is allowed to settle, the mixture is filtered and the precipitate is washed with ether/n-heptane 1:1. The precipitate is dried under high vacuum. This gives ethyl 3-[2-(2-methoxyethoxy)-5-nitropyridin-4-yl]-2-oxopropionate potassium salt as a red solid. (LC-MS protonate form) C13H16N2O7 (312.28), MS (ESI): 313 (M+H+).

Workup

additionadded dropwise over a period of 45 min
filtrationthe mixture is filtered
washthe precipitate is washed with ether/n-heptane 1:1
customThe precipitate is dried under high vacuum

Sources & evidence

ORD record: ord-93c2fb5a97904574b1b74696e84b3765
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048901B2

Reaction notes

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