The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reduction of α-furyl ketones by chemical methods at different potentials. Properties and physical-chemical studies of the different compounds obtained》. Authors are Morizur, Jean Pierre; Wiemann, Joseph.The article about the compound:1-(Furan-2-yl)propan-1-onecas:3194-15-8,SMILESS:O=C(C1=CC=CO1)CC).Electric Literature of C7H8O2. Through the article, more information about this compound (cas:3194-15-8) is conveyed.
α-Furyl alkyl ketones were reduced by Zn (E0 0.75 v.) in AcOH, Mg (E0 = 2.5 v.) in AcOH, and Na amalgam (E0 = 2.7 v.) in H2O. The products were characterized by infrared (IR) and nuclear magnetic resonance (NMR) spectra. The following ketones were prepared by known methods [alkyl group and b.p. (mm.) given]: Me (I), 69° (15); Et (II), 74-6° (11); Pr (III), 96° (20). To a stirred suspension of 50 g. Zn in 500 ml. H2O at 50° was added over 3 hrs. 1 mole ketone in 100 g. AcOH simultaneously with 50 g. Zn and the mixture stirred 1 hr. to give the following results. I gave 2.5 g. IV, b0.05 80-2°, m. 121-2° (benzene), and 27.5 g. 2,3-di-2-furylbutane-2,3-diol (V), b0.05 92-4°. II and III gave, resp., 25 g. 3,4-di-2-furylhexane-3,4-diol (VI), b0.05 96-8°, and 28 g. 4,5-di-2-furyloctane-4,5-diol (VII), b0.05 104-6°. To a stirred mixture of 1 mole ketone in 500 ml. H2O at 100°, 72 g. Mg was added in small portions with dropwise addition of 400 g. 90% AcOH over 6 hrs. to give (from I) 5 g. IV, 27 g. V, and 32 g. VIII (R = Me), b0.05 102-5°, (from II) 30 g. VI, 36 g. VIII (R = Et), b0.05 106-9°, and (from III) 15 g. VII, 18 g. VIII (R = Pr), b0.05 111-13°. One mole I was reduced at -35° by 34.5 g. Na as an amalgam ( CA 55, 363d) to give 8 g. IV, 7 g. V, m. 47-8°, and 3 g. VIII (R Me). Hydrogenation of IV by LiAlH4 in ice-cold Et2O gave IX, m. 98-100° (benzene). Similar treatment of the γ-ketols gave dihydroxy compounds melting over a 30-40° range.
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Reference:
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