The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Condensation of carboxylic acid esters with ethoxyacetylene》. Authors are Krasnaya, Zh. A.; Kucherov, V. F..The article about the compound:Ethyl 3-Ethoxy-2-Propenoatecas:1001-26-9,SMILESS:O=C(OCC)/C=C/OCC).Recommanded Product: Ethyl 3-Ethoxy-2-Propenoate. Through the article, more information about this compound (cas:1001-26-9) is conveyed.
To 7.4 g. HCO2Et was added with ice-cooling 6.4 ml. BF3.Et2O, followed by 3.5 g. EtOC:CH and, after 15 min., aqueous NaOAc to yield 31% EtOCH:CHCO2Et, b13 80-2°, n20D 1.4400. Similar reaction of EtOAc gave 29% EtOCMe:CHCO2Et (I), b7 70-2°, n20D 1.4460, m. 30-1°. Iso-BuCO2Et gave a mixture of products from which was isolated, with difficulty, some pure iso-BuC(OEt):CHCO2Et, b4 83-5°, n20D 1.4510. EtOCCH and BF3.Et2O in Et2O with ice-cooling gave in 15 mill. some EtOAc, AcCH2CO2Et, and I. Treatment of BzOMe with BF3 and EtOCCH as above gave 6% Et β-methoxycinnamate, b0.1 78-82°, n20D 1.5210. AcCH2CO2Et in this reaction gave 24% EtO2CCH:CMeCH2CO2Et, b13 124-6°; saponification with aqueous alc. KOH gave mixed cis- and trans-β-methylglutaconic acid, m. 90-107°, from which the trans form, m. 136-8°, was isolated by recrystallization from C6H6.
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Reference:
Bromide – Wikipedia,
bromide – Wiktionary