Ethyl pyruvate → HCID 90192601, compound
Reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.CCCCCC.[O:18]=[C:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21].[Cl-].[NH4+]>C1COCC1>[OH:18][C:19]([C:4]1[S:3][C:2]([CH3:1])=[N:6][CH:5]=1)([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1.5 g of 2-methyl-1,3-thiazole in 20 ml of THF was added 5.5 ml of a 2.76 M n-butyllithium/hexane solution at −78° C., followed by stirring for 30 minutes. To the reaction mixture was added dropwise a solution of 2 ml of ethyl 2-oxopropanoate in 10 ml of THF, followed by stirring at −78° C. for 1 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.05 g of ethyl 2-hydroxy-2-(2-methyl-1,3-thiazol-5-yl)propanoate.
Workup
- stirringby stirring at −78° C. for 1 hour
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was then evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-c7f68296e39e469492dc7e9b12e87f93
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278968B2
Reaction notes
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