ethyl 1,2,5,6-tetrahydro-3-hydroxy-2-oxopyridine-4-carboxylate synthesis
- Product Name:ethyl 1,2,5,6-tetrahydro-3-hydroxy-2-oxopyridine-4-carboxylate
- CAS Number:21472-88-8
- Molecular formula:C8H11NO4
- Molecular Weight:185.18
Yield:21472-88-8 72%
Reaction Conditions:
with potassium ethoxide in ethanol;toluene at 20 - 90;
Steps:
1.g Synthesis of Ethyl 5-hydroxy-6-oxo-1 ,2,3,6-tetrahydropyridine-4-carboxylate
2-pyrrolidinone (76 ml_,1 mol) and diethyl oxalate (140 mL, 1.03 mol) was dissolved in 1 L toluene at room temperature. Potassium ethoxide (EtOK) (24% in EtOH, 415 mL,1 .06 mol) was added, and the reaction mixture was heated to 90 °C.200 mL EtOH was added portion wise during the first hour of the reaction due to thickening of the reaction mixture. The reaction mixture was stirred overnight and cooled to room temperature. 210 mL HCI (5M, aq) was added slowly while stirring. 200 mL brine and 200 mL toluene was added, and the phases were separated.The aqueous phase was extracted with 2x400 mL CHC . The combined organic phases were dried (Na2S04), filtered and reduced in vacuo. The residue was recrystallized from EtOAc, giving the title compound as a pale yellow solid.Yield: 132.7g, 0.72 mol, 72%.
References:
WO2016/96843,2016,A1 Location in patent:Page/Page column 48
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