Publication details
A Simplified Method for the Efficient Preparation of Pivaloylacetonitrile
| Authors | |
|---|---|
| Year of publication | 2014 |
| Type | Article in Periodical |
| Magazine / Source | ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL |
| MU Faculty or unit | |
| Citation | |
| Doi | http://dx.doi.org/10.1080/00304948.2014.922386 |
| Field | Organic chemistry |
| Keywords | Nitriles; Synthesis of Organic Molecules; Catalysis; Green and Sustainable Chemistry; Waste Management AT SOURCE |
| Description | Pivaloylacetonitrile is a crucial intermediate for the synthesis of the isoxazole skeleton of the selective herbicide isouron and for the construction of inhibitors of p38 MAP kinase based on pyrazolyl ureas. The current method of synthesis is based on the nucleophilic substitution of halogen of 1-chloro- or 1-bromopinacolone by alkali metal cyanide in protic solvents. In the course of substitution reaction occurs but the 2-tert-butyloxirane-2-carbonitrile as a side-product in an amount of 20-35% and by-products of the condensation reaction of the corresponding 1-halopinacolone and emerging pivaloylacetonitrile, all due to non-selective action of cyanide. Our sophisticated solution of this problem is based on the addition of a catalytic amount of alkali iodide, leading to the suppression of undesirable side reactions and to obtain pivaloylacetonitrile in 95% yield with a purity of 99%. Explanation of the effect of added alkali iodide to increase the selectivity of the process being carried out. |
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