The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Furyl alkyl ketones》. Authors are Monoya, K..The article about the compound:1-(Furan-2-yl)propan-1-onecas:3194-15-8,SMILESS:O=C(C1=CC=CO1)CC).Related Products of 3194-15-8. Through the article, more information about this compound (cas:3194-15-8) is conveyed.
For the study of the relation between the chem. constitation of furyl alkyl ketones and their optical properties and also of the chem. action of alkyl nitrites and Na toward the ketones, the present study was carried out by M. The furyl alkyl ketones were prepared from furfural nitrite by the methods of Blaise (Compt. rend. 132, 38; 133, 299) and Kabina and Murayama, viz., Mg and the alkyl halide in dry Et2O was added to the nitrite in Ft2O; after the reaction was completed, the whole mixture was warmed, treated with H2SO4 and little H2C2O4 and then decomposed with steam. Thus, the following substances were prepared: C4H3O.COMe, C4H3OCOEt, C4H3OCOPr, iso-BuCOC4H3O, iso-AmCOC4H3O. Ethyl furoyldimethylacetate, light yellow liquid, b20 138-41°; furyl benzyl ketone, plates, m. 47-8°, solublein Et2O, difficultly sel. in alc.; oxime, m. 125-6°, soluble in alc., Et2O, petr. ether, C6H6; semicarbozone, m. 171-2°, difficultly soluble in alc. and insoluble in H2O. M. got pure ketones by transforming them into their oximes. During the preparation of furyl isobutyl and furyl isoamyl ketones, M. succeeded in isolating ketamines corresponding to each ketone, as a double salt with NH4Cl, (C4H3O.C(:NH)C4H9)2NH4Cl, m. 285-91°; (C4H30C(:NH)C5H11)2-NH4Cl, m. 268-70°, which by treatment with HCl easily yield ketones. So, the formation of ketone from nitrite may be represented by the following scheme: RCN + R’MgBr → RCR’:N.MgBr → RR’C:NH → RCOR’. The optical properties of the ketones studied by M. are shown in the table: , d4., nD., Mol. reference, Exaltation.;C4H3OCOMe ……………, 1.0977 (29.3°), 1.50177, 29.57, 1.14;C4H3O.COEt………………, 1.0587(29.5°), 1.49623, 34.25, 1.20;C4H3O.COPr………………, 1.0416(11.4°), 4.49970, 38.97, 1.31;C4H3O.COC4H9……………, 1.0160(14.6°), 1.49488, 43.64, 1.36;C4H3O.COC5H11……………, 0.9988(11°), 1.49260, 48.31, 1.41; The exaltation of the ketones increases with increasing mol. weight The action of alkyl nitrite and Na on the ketones was studied carefully by M. 7 g. furyl benzyl ketone in 50 cc. absolute Et2O and 3.5 g. EtNO2 and 0.8 g. Na at -13°, were neutralized with 1% NaOH, extracted with Et2O, and the H2O solution saturated with CO2 and then acidified with HCl, successively. 2 g. Et pyromucate, 1.4 g. pyromucic acid, 1.6 g. β-benzaldoxime and 1 g. isonitrosodesoxybenzofuroin, m. 127-30°, were isolated and identified. M. also obtained valeraldoxime from furyl amyl ketone. On applying the same reactions to the other ketones, he obtained the following results: , Ester., Free acid., Isonitroso compounds, Aldoxime.;PhCOBz;-10° ……………….., 37.6%, 28.1%, 28.3%, 16;5-10°………………, 11.4%, 38.6%, 40.1%, small;15°………………, 13.7%, 41.1%, 43.6%, small;PhCOEt………………, 10.5%, 50.5%, 24.7%, ..;PhCH:CHCH:CHCOMe……….., …., 30%, …., ..; By the action of AmNO2 and Na on menthone was obtained 2,6-dimethyl-3-ketoöctoic acid, isolated as the semicarbazone, m. 151-2°. The mechanism of the reaction between alkyl nitrite and Na and furyl ketone, may be represented in the following scheme:
I hope my short article helps more people learn about this compound(1-(Furan-2-yl)propan-1-one)Related Products of 3194-15-8. Apart from the compound(3194-15-8), you can read my other articles to know other related compounds.
Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem