US 11,866,386 B2
Non-cryogenic, ammonia-free reduction of aryl compounds
Kazunori Koide, Pittsburgh, PA (US); and James Proviano Burrows, West Homestead, PA (US)
Assigned to University of Pittsburgh—Of the Commonwealth System of Higher Education, Pittsburgh, PA (US)
Filed by University of Pittsburgh—Of the Commonwealth System of Higher Education, Pittsburgh, PA (US)
Filed on Sep. 17, 2021, as Appl. No. 17/477,900.
Claims priority of provisional application 63/080,205, filed on Sep. 18, 2020.
Prior Publication US 2022/0089508 A1, Mar. 24, 2022
Int. Cl. C07B 31/00 (2006.01); C07C 67/30 (2006.01); C07C 51/347 (2006.01); C07C 41/20 (2006.01)
CPC C07B 31/00 (2013.01) [C07C 41/20 (2013.01); C07C 51/347 (2013.01); C07C 67/30 (2013.01); C07C 2523/04 (2013.01)] 15 Claims
OG exemplary drawing
 
1. A method of reducing an aromatic ring or cyclic, allylic ether in a compound, comprising:
preparing a reaction mixture comprising a compound comprising an aromatic moiety or a cyclic, allylic ether moiety, an alkali metal, and either ethylenediamine, diethylenetriamine, thiethylenetetramine, or a combination thereof, in an ether solvent, wherein the ethylenediamine:compound molar ratio or the diethylenetriamine:compound molar ratio in the reaction mixture ranges from 2-20:1; and
reacting the reaction mixture at a temperature ranging from −20° C. to 30° C. for a time sufficient to reduce a double bond in the aromatic moiety to a single bond or to reduce the cyclic, allylic ether moiety.