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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 22
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Original Articles

Sigmatropic Rearrangement of Ammonium Ylides—Key Step in the Synthesis of Methyl 2-Formylphenyl Acetate

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Pages 3308-3317 | Received 05 May 2010, Published online: 26 Jul 2011
 

Abstract

N-Cyanomethyl-N,N-dimethyl-N-(α-methoxycarbonyl)benzylammonium salts 5 were synthesized and treated with different base/solvent systems, giving the products of sigmatropic rearrangements [2,3] 7 and [1,2] 8. In reactions carried out in liquid ammonia, [2,3] rearrangement definitively prevailed. Pure 7(or mixture of 7 and 8) were deprotected to afford methyl 2-formylphenyl acetate (9) in good yield.

Notes

a Estimated by GC in crude reactions mixtures.

b Yield of a crude mixture of 7 and 8.

c Results obtained in 12–15 experiments.

d Unidentified impurity formed in ca. 1–6% was removed under vacuum (ca. 20 °C/0.05 Torr).

e In some experiments 2–4% of aldehyde 9 was formed.

f Results obtained in three experiments.

g Results obtained in six experiments.

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