Ethanol → HCID 22033768, compound

Participants

Reaction Steps

In toluene (30 ml) was dissolved 1,1-cyclopropane dicarboaldehyde (2.94 g, 30 mmol). Under ice cooling and stirring, a solution of p-toluenesulfonate monohydrate (5.7 mg, 0.03 mmol) in ethanol (138 mg, 3.0 mmol), and then, ethyl orthoformate (4.67 g, 31.5 mmol) were added. The resulting mixture was stirred at the external temperature of 40° C. for 1 hour. After addition of a saturated aqueous solution (3 ml) of sodium bicarbonate to the reaction mixture, benzyl amine (3.54 g, 33 mmol) was added under ice cooling and stirring. At the same temperature, the mixture was stirred for 30 minutes. To the reaction mixture were added successively potassium cyanide (2.15 g, 33 mmol) and sodium bisulfite (4.69 g, 45 mmol), and then water (30 ml). The resulting mixture was stirred at room temperature for 13 hours. A saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate, filtered, and then evaporated under reduced pressure. The pale yellow oil thus obtained was subjected to chromatography on a silica gel column (silica gel; 150 g, hexane:ethyl acetate=10:1.) to give a colorless oil as the title compound (6.16 g, 71.2%).

Provenance & Evidence