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CAS No. : | 3788-94-1 | MDL No. : | MFCD06797311 |
Formula : | C9H14O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 186.21 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H227-H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
79% | With hydroxylamine In methanol; water at -5 - 30℃; for 2.5 h; Heating / reflux | Ethyl-5-methylisoxazole-4-carboxylate:Ethyl ethoxymethyleneacetoacetate, 110.00 g (0.59 mol) was taken in methanol (330 ml) and cooled to -5 0C and 50percent aqueous hydroxyl amine 39.03 g (0.59 mol on anhydrous basis) was added drop wise over a period of 1 hour at -5 to O0C. It was stirred for 30 minutes. The reaction mixture was allowed to attain temperature of 20 to 30 0C and then refluxed for 1 S hour. Solvent was removed under reduced pressure and the reaction mass was cooled to room temperature. n-Hexane (500 ml) was added and stirred for 30 minutes. Saturated sodium bicarbonate solution (100 ml) was added followed by water (400 ml) and stirred well. The organic layer was separated. The aqueous layer was re-extracted with n-hexane (2x200 ml). The combined organic layer was washed with water (2x250 ml). After removal of the solvent <n="8"/>72.5 g (79percent) of Ethyl-5-methylisoxazole-4-carboxylate was obtained as yellowish thick oil with 98.7 percent HPLC purity and having isomeric impurity less than 0.5 percent. |
78% | With hydroxylamine hydrochloride; sodium acetate In methanol; water at 0 - 20℃; | Solution of hydroxylamine hydrochloride (4.1 g, 0.059 mol) and sodium acetate (4.84 g, 0.059 mol) in water (10 ml) was added dropwise to a solution of compound 3 (11 g, 0.059 mol) in methanol (25 ml) at 0 °C. The mixture was stirred during overnight at room temperature followed by extraction with EtOAc (3 x 50 ml), the combined EtOAc extract was washed by aqueous sodium bicarbonate solution to minimize the impurities and dried over Na2SO4. After that the solvent was removed to afford 7.16 g (78 percent) of Ethyl-5-methylisoxazole-4-carboxylate as yellow oil, which was used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | at 130℃; for 5 h; | 2.22 Example 22 {prepared via Scheme 12)- 6-[(3-Cyclobutyl-2,3,4,5-tetrahydro-lH-3-benzazepin-7-yl)methyl]-2-(3-methoxyazetidin-l- yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one . iStep a) Intermediate 25Ethyl 2-(ethoxymethylene)-3-oxobutanoate A solution of ethyl 3-oxobutanoate (20 g, 154 mmol), triethylorthoformate (51.1 ml, 307 mmol), and acetic anhydride (43.5 ml, 461 mmol) was heated at 130 °C for 5 h. The reaction was cooled to r.t. and concentrated under reduced pressure to remove triethyl orthoformate and acetic anhydride. The remainder of acetic anhydride and triethyl orthoformate was removed by distillation (30 mbar, 30-70 °C). Ethyl 2-(ethoxymethylene)-3-oxobutanoate was distilled off (6 mbar, 80 °C to 128 °C) to leave ethyl 2-(ethoxymethylene)-3-oxobutanoate as a viscous yellow oil (22.8 g, 80percent) NMR (400 MHz, CDC13) δ 7.59 - 7.69 (m, 1H), 4.17 - 4.34 (m, 4H), 2.29 - 2.44 (m, 3H), 1.25 - 1.44 (m, 6H). |
79% | at 130℃; for 12 h; | Ethylacetoacetate (15.62 g, 0.12mol), triethylorthoformate (17.78 g, 0.12 mol), acetic anhydride (28.82 g, 0.24 mol) were mixed and heated at 130 oC for 12 hr with stirring. The product was distilled to obtain 11.4 g (79 percent) of black oil that was used directly in the next step. |
70% | at 135℃; | A mixture of ethyl acetoacetate (100 g, 0.77 mol), friethyi orthoformate ( 130 g, 0.92 mol), and acetic anhydride ( 150 g, 1 .5 mol) was heated ai 135 °C for 6 - 18 h in a round bottomed flask that was equipped with a distillation apparatus to collect the ethanol generated during the reaction. The reaction was cooled, concentrated and the residue was distilled under high vacuum to obtain the desired product (100 g, 70percent) as a pale yellow oil: ES MS m /z 181 [M + H]+. |
65% | at 130℃; for 4 h; | A mixture of compound 1 (10.41 g, 0.08 mol), triethyl orthoformate (14.23 g, 0.10 mol) and acetic anhydride (20.42 g, 0.20 mol) was heated at 130 °C for 4 h. The resulting EtOH, CH3CO2CH2CH3 and remaining materials were eliminated under reduced pressure and compound 2 (9.68 g) was obtained in 65percent yield. |
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