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CAS No. : | 65651-80-1 | MDL No. : | MFCD01075735 |
Formula : | C9H15NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VFFHLZJSZHWXAJ-VMPITWQZSA-N |
M.W : | 169.22 | Pubchem ID : | 639785 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
> 99% | With water; In neat (no solvent); at 20℃; for 0.166667h;Sealed tube; Green chemistry; | General procedure: Ethyl propiolate (0.5 mmol) was slowly added with stirring to amixture of N-methylaniline (0.6 mmol) and distilled H2O (0.1mL) in a 2 mL vial, and the vial then sealed. The mixture washeated at 80 C with stirring for 1 h. The reaction was thenquenched with sat. brine (0.5 mL), and the mixture was cooledto r.t. and extracted with EtOAc (3 × 1 mL) by pipette in thesame vial. The combined organic layers were dried (Na2SO4), filtered,and concentrated under reduced pressure. The residuewas purified by column chromatography [silica gel, PE-EtOAc(8:1)] to give a pale yellow oil |
86% | In toluene; at 23℃; for 12h; | To a solution of ethyl propiolate (2.96 mL, 29.6 mmol) in toluene (20 mL) was addeddropwise a solution of pyrrolidine (2.4 mL, 29.0 mmol) in toluene (5 mL). The mixture was stirred at 23 C for 12 h and concentrated. The residue was purified by flash chromatography (eluting gradient: 0-10% ethyl acetate in petroleum ether) to give (E)-ethyl 3-(pyrrolidin- 1- yl)acrylate as a yellow oil (4.2 g, 86%). ‘H NMR (400 MHz, CDC13) 0 7.63 (d, J = 12.8 Hz, 1H), 4.44 (d, J = 12.8 Hz, 1H), 4.10 (q, J =7.2 Hz, 2H), 3.37 - 3.10 (m, 4H), 2.02 - 1.97 (m,4H), 1.23 (t, J =7.2 Hz, 3H). |
In benzene; | EXAMPLE 73 Preparation of Ethyl β-Pyrrolidinylacrylate. A solution of 29.43 g of ethyl propiolate (0.30 mol) in 200 ml of benzene was held at 25 in a water bath with magnetic stirring. A solution of 21.34 g of pyrrolidine in 50 ml of benzene was added dropwise over a period of 45 minutes, during which time the temperature rose to 35. The clear brown solution was stirred overnight and the solvent under reduced pressure at 55. The residue was distilled under reduced pressure to give 35.05 g of yellow oil, boiling point 110 (0.4 torr), which crystallized upon standing. The yellow solid was recrystallized from petroleum ether to give 31.36 (62%) of yellowish platelets, m.p. 37.5-39.5. |
In benzene; | EXAMPLE 72 Preparation of Ethyl β-Pyrrolidinylacrylate. A solution of 29.43 g of ethyl propiolate (0.30 mol) in 200 ml of benzene was held at 25 in a water bath with magnetic stirring. A solution of 21.34 g of pyrrolidine in 50 ml of benzene was added dropwise over a period of 45 minutes, during which time the temperature rose to 35. The clear brown solution was stirred overnight and the solvent removed under reduced pressure at 55. The residue was distilled under reduced pressure to give 35.05 g of yellow oil, boiling point 110 (0.4 torr), which crystallized upon standing. The yellow solid was recrystallized from petroleum ether to give 31.36 (62%) of yellowish platelets, m.p. 37.5-39.5. |