title: 2-(Diethylamino)ethanethiol, a new reagent for the odorless deprotection of aromatic methyl ethers.
abstract: 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.
authors.affiliation: Research API, Pfizer Global R&D, 2800 Plymouth Road, Ann Arbor, MI 48105, USA. Javier.Magano@Pfizer.com
authors.forename: Javier
authors.initials: J
authors.lastname: Magano
authors.forename: Michael H
authors.initials: MH
authors.lastname: Chen
authors.forename: Jerry D
authors.initials: JD
authors.lastname: Clark
authors.forename: Thomas
authors.initials: T
authors.lastname: Nussbaumer
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D004987:Ethers / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D009812:Odorants; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D004987:Ethers; D005021:Ethylamines; D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds; C007638:ethanethiol; C520499:2-(diethylamino)ethanethiol