Hydrochloric Acid → Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoate
Reaction equation
C(O)C.[H-].[Na+].[N:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14]CC)=O)=[N:8][CH:7]=1.[C:17]([O:20][CH2:21][CH3:22])(=[O:19])[CH3:18].Cl.C(=O)(O)[O-].[Na+]>C(OCC)C.C1(C)C=CC=CC=1>[O:14]=[C:12]([C:9]1[CH:10]=[CH:11][N:6]=[CH:7][N:8]=1)[CH2:18][C:17]([O:20][CH2:21][CH3:22])=[O:19]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A solution of ethanol (16.18 g, 0.351 mol) in diethyl ether (15 ml) was added to a solution of sodium hydride (13.71 g, 0.343 mol, 60% in paraffin, paraffin was removed by washing with hexane) in diethyl ether (100 ml). After stirring the mixture for 30 min, the solvent was evaporated under reduced pressure, and toluene (100 ml) was added. A solution of ethyl pyrimidine-4-carboxylate (30.86 g, 0.203 mol) and ethyl acetate (30.48 g, 0.346 mol) in toluene (100 ml) was added, and the mixture was heated at 80° C. for 3 hrs. Hydrochloric acid was added, then sodium bicarbonate was added to adjust to pH 4. The solution was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give ethyl 3-oxo-3-(pyrimidin-4-yl)propionate (36.10 g, 92%).
Workup
- customthe solvent was evaporated under reduced pressure, and toluene (100 ml)
- additionwas added
- customThe solution was partitioned between water and ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-253c58475c6a4175b1d479b37f19e8f4
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07994315B2
Reaction notes
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