Reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=[O:8])[CH3:7].[C:9](=O)([O:12]C)[O:10][CH3:11].[H-].[Na+].Cl>C(OCC)(=O)C.O.O1CCCC1>[O:8]=[C:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[CH2:7][C:9]([O:10][CH3:11])=[O:12]Participants
Procedure
To 50 mL of a tetrahydrofuran solution containing 5.0 g of 1-(1,3-thiazol-2-yl)ethanone, 6.3 mL of dimethyl carbonate and 3.0 g of 60% sodium hydride were added at 10° C. The temperature of the reaction mixture was increased to room temperature, and the mixture was stirred for 16 hours. Thereto was further added 0.75 g of 60% sodium hydride, and the mixture was stirred for 4 hours. Water and ethyl acetate were then added thereto, and the reaction mixture was adjusted to pH 3.0 with 6 mol/L hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to obtain 2.3 g of a yellow oily substance, methyl 3-oxo-3-(1,3-thiazol-2-yl)propionate.
Workup
- additionwere added at 10° C
- stirringthe mixture was stirred for 4 hours
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washthe resultant solution was washed with an aqueous saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was removed under reduced pressure
- customThe residue thus obtained
- customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]
Sources & evidence
- ORD record
- ord-9bc99bf9eb234b0e900278f272f508e6
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524738B2
Linked notes
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