Sodium Carbonate → 4-Ethoxybut-2-yn-1-ol

Participants

Reaction Steps

To a solution of 2-(4-ethoxy-but-2-ynyloxy)-tetrahydro-pyran (0.5 g, 2.52 mmol) in methanol (10 mL) was added p-toluenesulfonic acid monohydrate (p-TSOH) (0.086 g, 0.454 mmol). The reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture was poured into aqueous sodium carbonate and extracted with methyl acetate. The organic layers were combined, dried (Na2SO4) and concentrated. Silica gel chromatography (1-10% MeOAc/hexane) provided 0.2 g of 4-ethoxy-but-2-yn-1-ol as a clear oil.

Provenance & Evidence