tert-Butyl cyanoacetate synthesis

6synthesis methods

Product Name:tert-Butyl cyanoacetate
CAS Number:1116-98-9
Molecular formula:C7H11NO2
Molecular Weight:141.17

tert-butyl acetamidocyanoacetate synthesis: 2-Cyanoacetic acid (1.701 g, 20 mmol) was suspended in a cetonitrile (20 ml) and tert-butanol (2.391 ml, 25.00 mmol). To this, a solution of N,N′-Dicyclohexylcarbodiimide (4.54 g, 22.00 mmol) in DCM (22 ml) was added under stirring at RT. The reaction mixture was stirred for 30 minutes, then filtered through Celite, and the solvents were evaporated. Proton NMR analysis of the residue showed complete conversion to the product. The product, tert-butyl cyanoacetate was not purified, but was taken straight through to the next reaction.
1H NMR (400 MHz, CDCl 3 ) δ 3.37 (s, 2H), 1.50 (s, 9H).

372-09-8
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$20.00/25g

75-65-0 Synthesis

75-65-0
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$10.00/10ml

1116-98-9
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$8.00/5g

Yield:1116-98-9 86%

Reaction Conditions:

with dmap;dicyclohexyl-carbodiimide in dichloromethane at 0 - 20; for 5 h;Inert atmosphere;Reagent/catalyst;Temperature;

Steps:

7
Under argon, cyanoacetic acid (7.16 mmol) and t-butanol (6.51 mmol) are dissolved in anhydrous dichloromethane (30 mL) and cooled to 0° C. DCC (7.16 mmol) and DMAP (cat.) are added to the solution. The medium is stirred for 4 hours at 0° C. and 1 h at room temperature. The reaction mixture is filtered, then concentrated under reduced pressure. The thereby obtained is purified by column chromatography (SiO₂, 20% EtOAccyclohexane) in order to obtain the t-butyl ester as a colorless oil (86%). [0501] ¹H NMR (400 MHz, CDCl₃): δ 4.23 (q, J=6.5 Hz, 2H, H-3), 3.44 (s, 2H, H-2), 1.28 (t, J=6.5 Hz, 3H, H-4).

References:

Ducki, Sylvie;Bennis, Khalil;Eschalier, Alain;Busserolles, Jér?me;Lesage, Florian;Rodriguez, Nuno;Vivier, Delphine US2015/38466, 2015, A1 Location in patent:Paragraph 0500-0501

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5292-43-3 Synthesis