The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Action of mixed organomagnesium compounds on N-disubstituted amides of α-furoic acid》. Authors are Maxim, N.; Zugravescu, I.; Fulga, I..The article about the compound:1-(Furan-2-yl)propan-1-onecas:3194-15-8,SMILESS:O=C(C1=CC=CO1)CC).Category: benzoxazole. Through the article, more information about this compound (cas:3194-15-8) is conveyed.
In aromatic series of keto amides, BzNR2, the action of the Grignard reagent produces ketones except in the instance of BzNEt2, where PhMgBr gave in addition Ph3CNEtPh (Busch and Fleischmann, C. A. 4, 3237). The action of the Grignard reagent has been studied on furoylanilides prepared by the action of α- furoyl chloride (I) on PhNHMe, PhNHEt and Ph2NH. A mixture of 136 g. PhNHMe and 250 g. of anhydrous benzene was treated dropwise with 83 g. I. The filtered benzene solution was washed, dried and evaporated and the crude product was recrystallized from benzene or alc., yielding 90% of α-furoyl-N-methylanilide (II), C12H11NO2, m. 120°. Similarly were prepared the corresponding ethylanilide (III), m. 127°, and diphenylamide (IV), C17H13NO2, m. 157°, in 90 and 80% yields, resp. II (20 g.) was added portionwise with stirring to 35 g. EtMgBr in 160 g. Et2O and, after 12 h., the product was decomposed with 25% HCl. The Et2O layer yielded a crude product, b63 100-40°, which was washed with 30% HCl and extracted with Et2O, giving 4 g. of α- furyl Et ketone (V), b63 120°; semicarbazone, m. 172°. Treatment of II with iso-BuMgCl similarly gave α- furyl iso-Bu ketone (VI), b26 110°; semicarbazone, m. 174°. With III, EtMgBr and iso-BuMgCl gave only V and VI but the crude product obtained by the action of PhMgBr yielded α- furyl Ph ketone (VII), b25 197°, and the tertiary base, ethyl(furyldiphenylmethyl)aniline, C25H23NO, m. 181°. Treatment of III with o-MeC6H4MgBr gave the oily α- furyl o-tolyl ketone (VIII), C12H10O2, b22 177°. Similarly with IV, the Grignard reagents EtMgBr, iso-BuMgCl, o-MeC6H4MgBr and PhMgBr produced V, VI, VIII and VII. The behavior of the furyl series of keto amides is thus analogous to that of the aromatic series in every respect.
Different reactions of this compound(1-(Furan-2-yl)propan-1-one)Category: benzoxazole require different conditions, so the reaction conditions are very important.
Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem