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CAS No. : | 2591-86-8 | MDL No. : | MFCD00006483 |
Formula : | C6H11NO | Boiling Point : | - |
Linear Structure Formula : | HCON(CH2CH2)2CH2 | InChI Key : | FEWLNYSYJNLUOO-UHFFFAOYSA-N |
M.W : | 113.16 | Pubchem ID : | 17429 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P280-P305+P351+P338-P312 | UN#: | 2810 |
Hazard Statements: | H302-H311-H319 | Packing Group: | Ⅲ |
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 |
---|---|---|
With n-butyllithium; In tetrahydrofuran; | Step 1 5-chloro-2-methylbenzaldehyde To a solution of <strong>[27139-97-5]2-bromo-4-chlorotoluene</strong> (20.0 g; 97.3 mmol) in 300 mL of THF at -78° C. was added dropwise a 2.5 M solution of n-BuLi (102.2 mmol). After 30 min of stirring at that temperature, 1-formylpiperidine (11.4 mL) in 10 mL of THF was added and the solution left for 1 h. It was brought to 0° C., quenched with NH4OAc (25percent) and diluted with EtOAc. The organic phase was dried over Na2SO4, filtered and the solvent removed to yield 13.3 g of the title compound. 1H NMR (CDCl3) delta2.6 (3H, s), 7.15 (1H, d), 7.4 (1H, d), 7.75 (1H, s) and 10.2 (1H, s). | |
13.3 g (89%) | With n-butyllithium; In tetrahydrofuran; | Step 1 Ethyl (E)-3-(5-chloro-2-methylphenyl)-2-propenoate To 2-bromo-4-chloro toluene (20.0 g; 97.3 mmol) in 300 mL of THF at -78° C. was added n-BuLi 2.5M (40.8 mL) dropwise. After 20 min. 1-formylpiperidine (11.4 mL; 103.0 mmol) in 10 mL of THF was added dropwise. After 30 min the reaction mixture was brought to 0° C. and quenched with HCl (10percent) and diluted with EtOAc. The organic phase was collected, dry and the solvent evaporated to yield 13.3 g (89percent) of 5-chloro-2-methylbenzaldehyde. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With chitosan; In neat (no solvent); at 75℃; for 0.05h;Microwave irradiation; Green chemistry; | General procedure: An equimolar mixture of <strong>[54396-44-0]2-methyl-3-(trifluoromethyl)aniline</strong> (0.351 g, 0.002 mol), corresponding aldehyde (0.002 mol), dimethyl phosphite (0.18 ml, 0.002 mol) and chitosan catalyst (10 molpercent) were taken in a reaction glass tube, degassed for 10 min and microwave irradiated at 180 W for 2 min at 60 °C. The progress of the reaction was monitored by TLC using petroleum ether and ethyl acetate (3:7) as solvent. After completion of the reaction, the mixture was diluted with ethyl acetate, washed with water (2 x 15 ml) followed by brine (1 x 10 ml), dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silicagel (100-200 mesh) by using a 7:3 mixture of ethyl acetate in hexane to afford the pure alpha-aminophosphonates. |
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