Water → Methyl 3-(3-methylpyrazin-2-yl)-3-oxopropanoate

HRID 1721818Notes

Reaction equation

[C:1](=[O:6])([O:4][CH3:5])OC.[H-].[Na+].[C:9]([C:12]1[C:17]([CH3:18])=[N:16][CH:15]=[CH:14][N:13]=1)(=[O:11])[CH3:10].O>C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:18][C:17]1[C:12]([C:9](=[O:11])[CH2:10][C:1]([O:4][CH3:5])=[O:6])=[N:13][CH:14]=[CH:15][N:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

21.4 g of dimethyl carbonate was added dropwise to a stirred mixture of 5.7 g of sodium hydride and 100 ml of toluene at room temperature. Then the mixture was heated to 80° C. and a solution of 16.1 g of 2-acetyl-3-methylpyrazine in 75 ml of toluene was added dropwise and the mixture was stirred at 75° C. for one hour. The mixture was cooled, 100 ml of water was added and the mixture was acidified with glacial acetic acid. The organic phase was separated, dried (Na2SO4) and stripped of volatiles. The residue was flash chromatographed on silica gel, with a 9:1 v:v mixture of methyl chloride and ethyl acetate as eluent. The second set of fractions was stripped of solvent to give methyl 3-(3-methyl-2-pyrazinyl)-3-oxopropionate (31A), as a yellow oil.

Workup

temperatureThe mixture was cooled
customThe organic phase was separated
dry with materialdried (Na2SO4)
customchromatographed on silica gel, with a 9:1 v
additionv mixture of methyl chloride and ethyl acetate as eluent

Sources & evidence

ORD record: ord-0bd1519159ed45f3bf1295af264913b8
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04853027

Reaction notes

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