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CAS No. : | 40052-13-9 | MDL No. : | MFCD00191886 |
Formula : | C7H12O4 | Boiling Point : | No data available |
Linear Structure Formula : | (CH3)3CO2CCH2CO2H | InChI Key : | NGGGZUAEOKRHMA-UHFFFAOYSA-N |
M.W : | 160.17 | Pubchem ID : | 545853 |
Synonyms : |
|
Chemical Name : | 3-tert-Butoxy-3-oxopropanoic acid |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hafnium(IV) chloride tetrahydrofuran complex; at 20℃; for 48h; | A 200 mL round-bottom flask equipped with a stirring bar was charged with compound 6 (3.0 g, 18.7 mmol) and methyl alcohol (70 mL). To the solution, hafnium(IV) chloride tetrahydrofuran complex (1:2) (88 mg, 0.19 mmol) was added. The reaction was allowed to stir for 2 days at room temperature. To the reaction mixture, brine was added and extracted with CH2Cl2 (3*), dried over MgSO4, and concentrated in vacuo. The remaining residue was purified by silica gel column chromatography (hexanes/AcOEt = 50:50) to afford the desired product 7 (3.0 g, 91percent) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 3.74 (s, 3H), 3.30 (s, 2H), 1.47 (s, 9H); 13C NMR (100 MHz, CDCl3) delta 167.5, 165.8, 82.1, 52.3, 42.7, 27.9; HR-FAB MS calcd for C8H15O4 [M+H]+ 175.0883, found 175.0875. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A solution of 1H-benzo[d]imidazol-5-amine (1 eq.) and the respective aldehyde (1 eq.) in dry methanol (1-3 ml per mmol) was stirred at room temperature for 3 hours. After addition of mono-tert-Butyl malonate (1 eq.) and 1-isocyano-2-methylpropan-2-yl methyl carbonate (1 eq.) stirring was continued for 48 hours. The solvent was evaporated and the residue was purified by flash chromatography on silica gel using a CHCl3/MeOH gradient. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.12 g | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; for 2h;Reflux; | A solution of 3-(t-butoxy)-3-oxopropionic acid (CAS No. 40052-13-9) (1.41 g, 8.79 mmol, 1.1 equivalents), <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (CAS No. 56621-89-7) (1.00 g, 7.99 mmol, 1.0 equivalents), triethylamine (1.34 mL, 9.59 mmol, 1.2 equivalents) and EDC (1.84 g, 9.59 mmol, 1.2 equivalents) in DCM (20 mL) was heated to reflux for 2 hours. The reaction mixture was cooled down to room temperature. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with DCM. The organic layer was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (silica gel, 50%-100% ethyl acetate/n-heptane) to afford the title compound (2.12 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 1.52 (s, 9H), 3.42 (s, 2H), 4.01 (s, 3H), 8.76 (s, 2H), 9.52 (br. s, 1H). |
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