Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 1-(Furan-2-yl)propan-1-one, is researched, Molecular C7H8O2, CAS is 3194-15-8, about Furylalkynes. IX. Transformations of furylethynylcarbinol and its derivatives.Synthetic Route of C7H8O2.
A solution of EtMgBr, prepared from 65.4 g. EtBr, in 560 ml. dry tetrahydrofuran (THF) was added dropwise to a solution of acetylene in THF (C2H2 was bubbled into THF 0.5 hr. at 0°). Fresh distilled furfural (54 g.) in the same volume THF was added after 30 min., the mixture was stirred 6 hrs. with simultaneous addition of C2H2, kept overnight, and decomposed with dilute NH4Cl to give 62% Ia, b2 83-5°, n20D 1.5040. Acrylonitrile (2.67 g.) was added to a stirred mixture of 5 g. Ia in 1 ml. 4% KOH at <30°. The mixture was stirred 6 hrs. at room temperature, kept overnight, and extracted with Et2O to yield 79.1% Ib, b0.5 142°, n20D 1.4968. HCl (1-2 drops) was added carefully to a stirred mixture of 5 g. Ia and 4.1 g. vinyl ethyl ether at 0°. The mixture was stirred 1 hr. at 0°, then 1 hr. at room temperature, added to 50 ml. cold H2O, and extracted with Et2O to yield 64% Ic, b2 72°, n20D 1.4695. Ic (5 g.) in 50 ml. EtOH was hydrogenated in the presence of 0.01 g. Raney Ni at room temperature/atm. pressure to give 96% II, b1.5 55-7°, n20D 1.4420. Ic (5 g.), 25 ml. dioxane, 1.26 g. HNMe2, and 1.75 g. paraformaldehyde were boiled 18 hrs. in a sealed tube to yield 4.5 g. Id, b1.5 105-7°, n20D 1.4720. Similarly was prepared 40% Ie, b1 142-3°, n20D 1.4931. An ether solution of 5 g. Ic was added dropwise to a solution of EtMgBr (from 5.6 g. EtBr), the mixture was stirred 7 hrs. at room temperature, kept overnight, 2.7 g. cyclohexanone in the same volume of Et2O was added to the vigorously stirred reaction mixture at 0° which was then stirred 20 hrs. and decomposed with dilute NH4Cl to yield 32% If, b6 125-7°, n20D 1.4900. Active MnO2 (35 g.) was added gradually to a cold solution of 5 g. Ia in 150 ml. Et2O and the mixture stirred 1 hr. at room temperature to give 91% 3-(2-furyl)-1-propyn-3-one (III), m. 43-6°. III (2 g.) was hydrogenated in alc. solution at room temperature to yield 3-(2-furyl)propan-3-one; 2,4-dinitrophenylhydrazone m. 194-6° (aqueous EtOH). III (1 g.) was added to an ether solution of CH2N2 prepared from 5 g. nitrosomethylurea and the mixture was kept overnight to give 76.4% IV, m. 199-200° (benzene-petroleum ether); 2,4-dinitrophenylhydrazone m. 225-6° (EtOH). A mixture of 2 g. III, 1.6 g. Et2NH, and 50 ml. Me2CO was stirred 6 hrs. at room temperature, and kept overnight to yield 76.4% V, b1 142-4°. Similarly were prepared 85.2% VI, b3 150-5°, m. 79-80°, and VII, m. 88-90°. Cu2Cl2 (0.5 g.) and 6 ml. 30% aqueous EtNH2 was added to a cool solution of 3.7 g. Ia in MeOH, 5.5 g. PhC:CBr and 0.1 g. NH2OH.HCl was added, and the mixture was stirred 30 min. at the room temperature KCN (0.1 g.) in 3 ml. H2O was added, the mixture was added to water, extracted with Et2O; the organic layer was stirred 4 hrs. with 60 g. active MnO2 to give 6.5 g. VIII m. 85.5-6.5°. 6 references. The article 《Furylalkynes. IX. Transformations of furylethynylcarbinol and its derivatives》 also mentions many details about this compound(3194-15-8)Synthetic Route of C7H8O2, you can pay attention to it, because details determine success or failure
Reference:
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