The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reaction of methyl tetrahydropyromucate with aniline. XXXI》. Authors are Yur’ev, Yu. K.; Vendel’shtein, E. G..The article about the compound:Methyl tetrahydrofuran-2-carboxylatecas:37443-42-8,SMILESS:O=C(C1OCCC1)OC).Recommanded Product: 37443-42-8. Through the article, more information about this compound (cas:37443-42-8) is conveyed.
Passage of Me 2-furoate in a H atm. over Pd-asbestos at 160° gave 78% Me tetrahydro-2-furoate, b736 179.5-80.5°, n20D 1.4371, d204 1.1080. This (10 g.) and 27 g. PhNH2 passed in a N atm. over Al2O3 at 360° gave CO2, 14 g. PhNH2, and 1.5 g. 1-phenylpyrrolidine, b4 104-5°, n20D 1.5840, d204 1.0164; picrate, m. 116°. Passage of the ester at 360° over Al2O3 in a N atm. gave CO2, propene, and MeOH. Hydrolysis of the ester with 2 N NaOH 4 hrs. at reflux gave 76% free acid, a sirupy microcrystalline mass; this heated to 270-80° begins to lose CO2, which occurs freely at 300-5°, yielding furanidine, b755 65°, n20D 1.4088, d204 0.8899.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics