Sodium Thiosulfate → Ethyl 1-formylcyclopropanecarboxylate

Participants

Reaction Steps

At 0° C., 5.05 g (11.9 mmol) of Dess-Martin periodane reagent were added to a solution of 1.225 g (8.5 mmol) of ethyl 1-hydroxymethylcyclopropanecarboxylate [for the preparation see, for example, T. A. Ayers, Tetrahedron Lett. 40 (30), 5467-5470 (1999)] in 43 ml of dichloromethane, and the mixture was then stirred at RT for 6 h. A solution of 6.7 g (42.5 mmol) of sodium thiosulfate in 60 ml of saturated aqueous sodium bicarbonate solution was then added to the reaction mixture. The mixture was stirred at RT for 20 min, and the phases were then separated. The organic phase was washed twice with water, dried over magnesium sulfate and concentrated at 20° C. under reduced pressure. This gave 1.139 g (80.0% of theory) of the target compound.

Provenance & Evidence