Ethanol → HCID 10290795, compound

Participants

Reaction Steps

In a dried flask (300 ml volume), the inside of which had been flushed with nitrogen, were placed 2-methyl-2-tetrahydrofuranoxy-4-cyclopropyl-3-butyne (13.4 g, purity 97.5%, 67.3 mmol.) prepared in Example 4, ethanol (120 ml) and pyridinium p-toluenesulfonate (6.7 mg), and the resulting mixture was heated at 50° C. to 60° C. for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature, 10 mg of sodium methoxide (25% methanol solution) was added to the cooled mixture and ethanol was distilled through a rotary evaporator. To the concentrate obtained was added 100 ml of water, and the mixture was subjected to extraction with two 100 ml portions of ethyl acetate. The extract was washed with an aqueous saturated sodium bicarbonate solution and a saturated saline solution, dried over anhydrous sodium sulfate and concentrated by distillation of the solvent through a rotary evaporator to give 10.8 g of a crude product. The crude product was purified by silica gel column chromatography to give 2-methyl-2-hydroxy-4-cyclopropyl-3-butyne (7.84 g, purity 98.6%, yield 92.6%) having the following physical data:

Provenance & Evidence