ChemicalBook CAS DataBase List Ethyl 2-cyanopropanoate

Ethyl 2-cyanopropanoate synthesis

8synthesis methods

Product Name:Ethyl 2-cyanopropanoate
CAS Number:1572-99-2
Molecular formula:C6H9NO2
Molecular Weight:127.14

105-56-6
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74-88-4
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1572-99-2
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$14.00/1g

Yield:1572-99-2 83%

Reaction Conditions:

Stage #1:ethyl 2-cyanoacetate with sodium hydride in tetrahydrofuran;paraffin oil at 0; for 0.25 h;Inert atmosphere;
Stage #2:methyl iodide in tetrahydrofuran;paraffin oil at 0 - 20; for 3 h;Inert atmosphere;

Steps:

Ethyl 2-cyanopropanoate (40)
Sodium hydride (58 mg, 1.46 mmol, 0.33 equiv, 60% inparaffin) was suspended in dry THF (1.46 mL) and stirredunder N2 at 0 °C. A solution of ethyl-2-cyano-acetate (500mg, 4.42 mmol, 1.0 equiv) in THF (0.737 mL) was addedusing a syringe. After 15 min stirring at 0 °C, iodomethane(90.8 μL, 207 mg, 1.46 mmol, 0.33 equiv) was added andreaction left stirring for 3 h. The reaction mixture was then quenched with water (10 mL),diethyl ether (10 mL) added and the separated organic layer was washed with brine (3 × 25mL). The organic layer was dried over Na2SO4 und the solvent was removed under reducedpressure. The product was then purified using a silica column with a solvent mixture of 5%(EtOAc/hexane) and the desired nitrile was recovered as a colourless liquid (51 mg, 83% yield).

References:

Mallia, Carl J.;Englert, Lukas;Walter, Gary C.;Baxendale, Ian R. [Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 875 - 883] Location in patent:supporting information

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