2-(Diethylamino)ethanethiol, a New Reagent for the Odorless Deprotection of Aromatic Methyl Ethers

Javier Magano,* Michael H. Chen, Jerry D. Clark, and Thomas Nussbaumer
Research API, Pfizer Global R&D, 2800 Plymouth Road, Ann Arbor, Michigan 48105, and CarboGen AG, Schachenallee 29, CH-5001 Aarau, Switzerland. Javier.Magano@Pfizer.com
J. Org. Chem., 2006, 71 (18), pp 7103–7105
DOI: 10.1021/jo0611059
Publication Date (Web): August 11, 2006
Copyright © 2006 American Chemical Society

Abstract

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A new reagent for the deprotection of aromatic methyl ethers, 2-(diethylamino)ethanethiol, is reported. This compound, commercially available as its HCl salt, affords the corresponding phenols in good to excellent yields on a wide variety of substrates. A clear advantage of this method over the use of more common thiols, such as ethanethiol, is the easy extraction of both the deprotecting reagent and the byproduct 2-(diethylamino)ethyl methyl sulfide into the aqueous phase by quenching with dilute acid, which allows an essentially odorless workup.

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History

  • Published In Issue September 01, 2006
  • Received May 30, 2006

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