Pyridine as a Borane Scavenger to Avoid Overreduction During the Conversion of Acid Chlorides to the Corresponding Aldehydes Using Sodium Borohydride
James H. Babler
Synthetic Communications 12(11), 839-846 (1982) (https://www.thevespiary.org/rhodium/Rhodium/chemistry/nabh4-py.cocl.cho.html)
(https://www.thevespiary.org/rhodium/Rhodium/chemistry/nabh4-py.cocl.cho.html)
Abstract
By use of sodium borohydride in N,N-dimethylformamide solution containing a molar excess of pyridine as a borane scavenger, direct conversion of both aliphatic and aromatic acid chlorides to the corresponding aldehydes can be achieved in >70% yield with minimal (5-10%) alcohol formation.