ChemicalBook CAS DataBase List 2,2-DIMETHYLCYANOACETATE METHYL ESTER

2,2-DIMETHYLCYANOACETATE METHYL ESTER synthesis

8synthesis methods

Product Name:2,2-DIMETHYLCYANOACETATE METHYL ESTER
CAS Number:72291-30-6
Molecular formula:C6H9NO2
Molecular Weight:127.14

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72291-30-6

The general procedure for the synthesis of methyl 2-cyano-2-methylpropionate from methyl cyanoacetate and iodomethane is as follows: 1. In a dry reaction flask, methyl cyanoacetate (15 mL) and iodomethane (200 g) were added with potassium carbonate as base and acetone as solvent. 2. The reaction mixture was heated to reflux with continuous stirring for 4 days. 3. Upon completion of the reaction, insoluble potassium carbonate was removed by filtration. 4. The acetone in the filtrate was removed by distillation to obtain the crude product. 5. The crude product was purified by vacuum distillation (pressure: 16 mmHg, temperature: 76°C) to give methyl 2-cyano-2-methylpropionate (19.5 g, 73% yield). Product characterization data: 1H NMR (270 MHz, CDCl3) δ: 1.62 (s, 6H), 3.83 (s, 3H). 13C NMR (67.5 MHz, CDCl3) δ: 24.6, 38.4, 121.0, 170.0.

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Yield: 73%

Reaction Conditions:

with potassium carbonate in acetone

Steps:

1 Synthesis of N-(N-4-amidinobenzoyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid STR7 (1) Methyl 2,2-dimethyl-cyanoacetate
EXAMPLE 1 Synthesis of N-(N-4-amidinobenzoyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid STR7 (1) Methyl 2,2-dimethyl-cyanoacetate Methyl cyanoacetate (15 ml) and methyl iodide (200 g) were stirred and refluxed under the presence of potassium carbonate in acetone for 4 days and the potassuim carbonate was then removed by filtration. Acetone was distilled off from the filtrate and the residue was distilled in vacuo (16 mmHg, 76° C.) to yield methyl 2,2-dimethyl-cyanoacetate (19.5 g, 73%). NMR: ¹ H (270 MHz, CDCl₃) 1.62, s, 6H: 3.83, s, 3H: ¹³ C(67.5 MHz, CDCl₃) 24.6, 38.4, 121.0, 170.0

References:

Nippon Steel Corporation;Nippon Steel Chemical Co., Ltd. US5866592, 1999, A