Diethyl Oxalate → Ethyl 3-(6-methoxy-3-nitropyridin-2-yl)-2-oxopropanoate
Reaction equation
[O-]CC.[K+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH3:23])[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][CH:18]=1>C(OCC)C.C(O)C>[CH2:13]([O:12][C:5](=[O:11])[C:6](=[O:8])[CH2:23][C:21]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][CH:18]=[C:17]([O:16][CH3:15])[N:22]=1)[CH3:14]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirred suspension of potassium ethoxide (0.55 g, 6.55 mmol) in diethyl ether (20 mL, anhydrous) and ethanol (4 mL) was added diethyl oxalate (894 μL, 6.55 mmol) and the reaction mixture was stirred for 30 min prior to the addition of 6-methoxy-2-methyl-3-nitropyridine (Preparation 33, 1.0 g, 5.95 mmol) in diethyl ether (8 mL). The resulting red suspension was stirred at rt, under argon, for 20 h. The mixture was filtered, the solid washed thoroughly with diethyl ether then dried. The red solid was then taken up in hot water and the solution cooled to 0° C. The precipitate was filtered, washed with cold water, and dried to give the title compound as a beige solid. δH (CDCl3): 1.40 (3H, t), 4.07 (3H, s), 4.39 (2H, q), 6.74 (1H, d), 7.57 (1H, s), 8.40 (1H, d), 13.82 (1H, s).
Workup
- stirringThe resulting red suspension was stirred at rt, under argon, for 20 h
- filtrationThe mixture was filtered
- washthe solid washed thoroughly with diethyl ether
- customthen dried
- filtrationThe precipitate was filtered
- washwashed with cold water
- customdried
Sources & evidence
- ORD record
- ord-0d6300623cc8437dabe82a0b0b01ab33
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158622B2
Reaction notes
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