Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system was written by Fujihira, Yamato;Liang, Yumeng;Ono, Makoto;Hirano, Kazuki;Kagawa, Takumi;Shibata, Norio. And the article was included in Beilstein Journal of Organic Chemistry in 2021.Electric Literature of C8H18O4 This article mentions the following:
A straightforward method that enables the formation of biol. attractive trifluoromethyl ketones RC(O)CF3 (R = naphthalen-2-yl, 4-chlorophenyl, 4-cyclohexylphenyl, etc.) from readily available Me esters RCOOCH3 using the potent greenhouse gas fluorophore (HCF3, HFC-23) was developed. The combination of fluoroform and KHMDS in triglyme at -40鎺矯 was effective for this transformation, with good yields as high as 92%. Substrate scope of the trifluoromethylation procedure was explored for aromatic, aliphatic, and conjugated Me esters. This study presents a straightforward trifluoromethylation process of various Me esters that convert well to the corresponding trifluoromethyl ketones. The tolerance of various pharmacophores under the reaction conditions was also explored. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Electric Literature of C8H18O4).
2,5,8,11-Tetraoxadodecane (cas: 112-49-2) 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).Electric Literature of C8H18O4
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem