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With dihydrogen peroxide; 10-methylacridinium perchlorate; In water; acetonitrile; at 20℃; for 20h;UV-irradiation;
General procedure A: Cyclobutanone (0.5 mmol) and AcrH+ClO4- (7.4 mg, 0.025 mmol) were dissolved in CH3CN (1 mL). Hydrogen peroxide (68 muL, 30% solution in water, 0.6 mmol) was added and the mixture was irradiated with a 450 W high-pressure mercury lamp in a Pyrex flask (lambda>320 nm) at room temperature for 20 h. The course of the reaction was monitored by TLC. After completion of the reaction, solvent was evaporated in vacuum. Purification of the residue by column chromatography (silica gel, ethyl acetate/petroleum ether gradient) yielded the corresponding lactone.
4-benzyl-3-[(5-methylfuran-2-yl)methylidene]-dihydrofuran-2(3H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With piperidine; In ethanol; at 20℃; for 1h;
General procedure: a. Piperidine, 0.0025 mol, was added to a solution of 0.01 mol of 5-alkylfuran-2(3H)-one 1 or 2 in 25 mL of ethanol, and 0.005 mol of furancarbaldehyde 3 was then added with stirring. The mixture was stirred for 1 h at room temperature and was then kept in a refrigerator for crystallization. The precipitate was filtered off, the mother liquor was evaporated by half, and the residue was kept in a refrigerator to obtain an additional amount of the product. The product was recrystallized from ethanol. b. A solution of 0.01 mol of dihydrofuran-2(3H)-one 6 or 7 and 0.005 mol of furancarbaldehyde 3 in10 mL of ethanol was cooled in an ice bath, and 2 mL(0.007 mol) of a 25% solution of sodium ethoxide in ethanol was added dropwise. Ethanol, 20 mL, was then added, and the mixture was stirred for 1.5 h at room temperature and for 2 h at 5060C until the initial aldehyde disappeared. The mixture was treated with 10% sulfuric acid to neutral reaction, stirred for 1 h, and evaporated by 50-70%. The residue was kept in a refrigerator, and the precipitate was filtered off and recrystallized from ethanol.
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