2-(Diethylamino)ethanethiol, a new reagent for the odorless deprotection of aromatic methyl ethers.
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.
Magano
Javier
J
Research API, Pfizer Global R&D, 2800 Plymouth Road, Ann Arbor, MI 48105, USA. Javier.Magano@Pfizer.com
Chen
Michael H
MH
Clark
Jerry D
JD
Nussbaumer
Thomas
T
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*
D004987:Ethers; D005021:Ethylamines; D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds; C007638:ethanethiol; C520499:2-(diethylamino)ethanethiol