Ring opening of 3-bromo-2-isoxazolines to β-hydroxy nitriles

Martin G. Kociolek, Kyle P. Kalbarczyk

Research output: Contribution to journal › Article

8 Citations (Scopus)

Abstract

3-Bromo-2-isoxazolines were converted to the corresponding β-hydroxy nitriles by treatment with sodium iodide in the presence of either chlorotrimethylsilane or para-toluenesulfonic acid. Both methods gave β-hydroxy nitriles under relatively mild conditions in good to moderate yields for a variety of substituted 3-bromo-2-isoxazolines.

Original languageEnglish (US)
Pages (from-to)4387-4394
Number of pages8
JournalSynthetic Communications
Volume34
Issue number23
DOIs
StatePublished - Dec 30 2004

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Nitriles
Sodium Iodide
4-toluenesulfonic acid
trimethylchlorosilane

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Kociolek, Martin G. ; Kalbarczyk, Kyle P. / Ring opening of 3-bromo-2-isoxazolines to β-hydroxy nitriles. In: Synthetic Communications. 2004 ; Vol. 34, No. 23. pp. 4387-4394.
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Kociolek, MG & Kalbarczyk, KP 2004, 'Ring opening of 3-bromo-2-isoxazolines to β-hydroxy nitriles', Synthetic Communications, vol. 34, no. 23, pp. 4387-4394. https://doi.org/10.1081/SCC-200039452

Ring opening of 3-bromo-2-isoxazolines to β-hydroxy nitriles. / Kociolek, Martin G.; Kalbarczyk, Kyle P.

In: Synthetic Communications, Vol. 34, No. 23, 30.12.2004, p. 4387-4394.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Ring opening of 3-bromo-2-isoxazolines to β-hydroxy nitriles

AU - Kociolek, Martin G.

AU - Kalbarczyk, Kyle P.

PY - 2004/12/30

Y1 - 2004/12/30

N2 - 3-Bromo-2-isoxazolines were converted to the corresponding β-hydroxy nitriles by treatment with sodium iodide in the presence of either chlorotrimethylsilane or para-toluenesulfonic acid. Both methods gave β-hydroxy nitriles under relatively mild conditions in good to moderate yields for a variety of substituted 3-bromo-2-isoxazolines.

AB - 3-Bromo-2-isoxazolines were converted to the corresponding β-hydroxy nitriles by treatment with sodium iodide in the presence of either chlorotrimethylsilane or para-toluenesulfonic acid. Both methods gave β-hydroxy nitriles under relatively mild conditions in good to moderate yields for a variety of substituted 3-bromo-2-isoxazolines.

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Kociolek MG, Kalbarczyk KP. Ring opening of 3-bromo-2-isoxazolines to β-hydroxy nitriles. Synthetic Communications. 2004 Dec 30;34(23):4387-4394. https://doi.org/10.1081/SCC-200039452

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