Ethanol → HCID 9815537, compound

Participants

Reaction Steps

In a dried flask (300 ml volume), the inside of which had been flushed with nitrogen, were placed 2,6-dimethyl-6-tetrahydrofuranoxy-8-cyclopropyl-7-octyne (10.72 g, purity 98.5%, 0.04 mol.) prepared in Example 2, ethanol (100 ml) and pyridinium p-toluenesulfonate (5.4 mg). The resulting mixture was heated at 50° C. to 60° C. for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and to the mixture was added 10 mg of sodium methoxide (25% methanol solution). Ethanol was removed by distillation through a rotary evaporator. To the concentrate obtained was added 100 ml of water and the resulting 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 10.1 g of a crude product. The crude product was purified by distillation under reduced pressure to give 2,6-dimethyl-6-hydroxy-8-cyclopropyl-7-octyne (7.33 g, purity 99.0%, yield 93.5%) having the following physical data:

Provenance & Evidence