Ethyl 4-(dimethylamino)-2-oxo-but-3-enoate → HCID 57799147, compound

HRID 2100361Notes

Reaction equation

Cl.[CH3:2][O:3][CH2:4][CH2:5][NH:6]N.[CH2:8]([O:10][C:11](=[O:19])[C:12](=O)[CH:13]=[CH:14][N:15](C)C)[CH3:9]>C(O)C>[CH2:8]([O:10][C:11]([C:12]1[N:6]([CH2:5][CH2:4][O:3][CH3:2])[N:15]=[CH:14][CH:13]=1)=[O:19])[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

2-Methoxyethylhydrazine hydrochloride (Ref: J. Med. Chem. (1967) 11 (1) 79-83) (1.07 g, 8.5 mmol) and ethyl-4-dimethylamino-2-oxo-but-3-enoate (1.5 g, 8.5 mmol) were dissolved in ethanol (10 ml) and heated at 60° C. for 7 hours. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate (80 ml) and dilute sodium carbonate solution (40 ml). The organic layer was dried over anhydrous Na2SO4 and the solvent removed in vacuo to give a brown gum. This material was chromatographed on silica gel (30 g) using 40% to 20% heptane in ethyl acetate. The higher running product was collected to give 2-(2-methoxyethyl)-2H-pyrazole-3-carboxylic acid ethyl ester as 750 mg of a mobile yellow oil. The lower running product was collected to give 1-(2-methoxyethyl)-1H-pyrazole-3-carboxylic acid ethyl ester as 360 mg of a yellow oil.

Workup

customThe solvent was evaporated in vacuo
customthe residue was partitioned between ethyl acetate (80 ml) and dilute sodium carbonate solution (40 ml)
dry with materialThe organic layer was dried over anhydrous Na2SO4
customthe solvent removed in vacuo
customto give a brown gum
customThis material was chromatographed on silica gel (30 g)
customwas collected

Sources & evidence

ORD record: ord-ca9d32ab03e44d54b52dc9c927f39d05
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572797B2

Reaction notes

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