US 12,421,178 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 Nov. 28, 2023, as Appl. No. 18/521,250.
Application 18/521,250 is a division of application No. 17/477,900, filed on Sep. 17, 2021, granted, now 11,866,386.
Claims priority of provisional application 63/080,205, filed on Sep. 18, 2020.
Prior Publication US 2024/0092708 A1, Mar. 21, 2024
Int. Cl. C07C 31/00 (2006.01); C07B 31/00 (2006.01); C07C 5/10 (2006.01); C07C 41/20 (2006.01); C07C 51/347 (2006.01); C07C 67/30 (2006.01)
CPC C07B 31/00 (2013.01) [C07C 5/10 (2013.01); C07C 41/20 (2013.01); C07C 51/347 (2013.01); C07C 67/30 (2013.01); C07C 2523/04 (2013.01)] 18 Claims
OG exemplary drawing
 
1. A method of reducing an aromatic ring or a 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, an alcohol, and either ethylenediamine or diethylenetriamine, in an ether solvent; and
reacting the reaction mixture at 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.