In 2022,EL-Mahdy, Ahmed F. M.; Bakhite, Etify A.; Abdel-Hafez, Shams H.; Ibrahim, Omaima F.; Abdu-Allah, Hajjaj H. M.; Marae, Islam S. published an article in Journal of Heterocyclic Chemistry. The title of the article was 《Synthesis, characterization, and photophysical properties of some new thieno[2,3-b]pyridines bearing phenylethenyl moiety》.Synthetic Route of C6H12O3 The author mentioned the following in the article:
The 5-acetyl-3-cyano-6-methyl-4-(2-phenylethenyl)pyridine-2(1H)-thione was synthesized by interaction of cinnamylidene-2-cyanothioacetamide and acetylacetone or via one-pot reaction of E-cinnamaldehyde, 2-cyanothioacetamide, and acetylacetone. Reaction of 5-acetyl-3-cyano-6-methyl-4-(2-phenylethenyl)pyridine-2(1H)-thione with Et iodide or N-chloroacetyl derivative of aromatic amines RC6H4NHC(O)CH2Cl (R = Me, OMe, acetyl, Cl) in boiling ethanol containing sodium ethoxide gave the 5-acetyl-3-cyano-2-ethylsulfanyl-6-methyl-4-(2-phenylethenyl)pyridine and 5-acetyl-3-amino-2-(N-arylcarbamoyl)-6-methyl-4-(2-phenylethenyl)thieno[2,3-b]pyridines I, resp. Compound I (R = Cl) was reacted with 2,5-dimethoxytetrahydrofuran or tri-Et orthoformate to furnish 5-acetyl-2-[N-(4-chlorophenyl)carbamoyl]-6-methyl-4-(2-phenylethenyl)-3-(1H-pyrrol-1-yl)- thieno[2,3-b]pyridine or 8-acetyl-3-(4-chlorophenyl)-7-methyl-9-(2-phenylethenyl)pyrido [3′,2′:4,5]thieno[3,2-d]pyrimidine-4(3H)-one, resp. The photophys. properties of I (Me, OMe, Cl), and 8-acetyl-3-(4-chlorophenyl)-7-methyl-9-(2-phenylethenyl)pyrido [3′,2′:4,5]thieno[3,2-d]pyrimidine-4(3H)-one were fully studied and the obtained results included herein. The fluorescence data confirmed that compounds I (Me, OMe, Cl), and 8-acetyl-3-(4-chlorophenyl)-7-methyl-9-(2-phenylethenyl)pyrido [3′,2′:4,5]thieno[3,2-d]pyrimidine-4(3H)-one exhibit aggregation-induced emission behavior with high absolute quantum yields. In the experimental materials used by the author, we found 2,5-Dimethoxytetrahydrofuran(cas: 696-59-3Synthetic Route of C6H12O3)
2,5-Dimethoxytetrahydrofuran(cas: 696-59-3) is a member of ether. Friedel Crafts reaction, for example, adds an alkyl or acyl group to aromatic ethers when they react with an alkyl or acyl halide in the presence of a Lewis acid as a catalyst.Synthetic Route of C6H12O3
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem