F–-Free Deoxyhydrotrifluoromethylation of α-Keto Esters with Ph3P+CF2CO2–: Synthesis of α-CF3-Substituted Esters was written by Zheng, Ying;Jia, Yimin;Yuan, Yuan;Jiang, Zhong-Xing;Yang, Zhigang. And the article was included in Journal of Organic Chemistry in 2020.Formula: C5H12O3 This article mentions the following:
Trifluoromethylated compounds are usually obtained via trifluoromethylation reaction by the use of CF3SiMe3 and NaSO2CF3, Umemoto’s and Togni’s reagents. Here, an external fluorine anion-free direct deoxyhydrotrifluoromethylation of α-keto esters with a difluoromethylating reagent has been achieved, in which the employment of water can promote the dissociation of the CF2 group to form a CF3 moiety, which provides the successful transformation. The current protocol demonstrates one of the most practical approaches to generate α-trifluoromethyl esters with a broad substrate scope and high functional group compatibility, in which it is applicable to late-stage modification of biol. active compounds and can be readily scaled up. Mechanistic investigation reveals that an in situ-generated gem-difluoroalkene intermediate is decomposed by water, giving rise to acid fluoride and HF. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Formula: C5H12O3).
2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Formula: C5H12O3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem