Rongalite-Mediated Transition Metal- and Hydride-Free Chemoselective Reduction of α-Keto Esters and α-Keto Amides was written by Golla, Sivaparwathi;Kokatla, Hari Prasad. And the article was included in Journal of Organic Chemistry in 2022.Formula: C7H7ClO This article mentions the following:
A transition metal- and hydride-free protocol was developed for the chemoselective reduction of α-keto esters and αketo amides using rongalite as a reducing agent. Here, rongalite acts as a hydride-free reducing agent via a radical mechanism. This protocol offered the synthesis of a wide range of α-hydroxy esters ArCHOHC(O)OR [Ar = Ph, 4-MeC6H4, 1-naphthyl, etc.; R = Et, i-Pr, Bn, etc.] and α-hydroxy amides ArCHOHC(O)NR1R2 [Ar = Ph, 4-MeC6H4, 4-MeOC6H4, etc.; R1 = H, Me; R2 = Ph, 4-MeC6H4, Bn, etc.] with 85-98% yields. This chemoselective method was compatible with other reducible functionalities such as halides, alkenes, amides and nitriles. The use of inexpensive rongalite (ca. $0.03/1 g), mild reaction conditions, and gram-scale synthesis were some of the key features of this methodol. Also, cyclandelate, a vasodilator drug, was synthesized in gram scale with 79% yield. In the experiment, the researchers used many compounds, for example, (4-Chlorophenyl)methanol (cas: 873-76-7Formula: C7H7ClO).
(4-Chlorophenyl)methanol (cas: 873-76-7) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Formula: C7H7ClO
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts