Sodium Bicarbonate → 6-(But-3-ynyloxy)hexanal

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Reaction Steps

6-Bromohexylbut-3-ynyl ether (525 mg) in DMSO (2 ml) was added to a mixture of sodium bicarbonate (1 g) in DMSO (8 ml) at 150° C. with vigorous stirring and nitrogen bubbling through the solution. The mixture was stirred for 20 min at 150° C. and then allowed to cool to room temperature, diluted with Et2O and washed with water. The aqueous layer was extracted with Et2O and the combined ether layers were washed with dilute hydrochloric acid, brine, dried (MgSO4) and evaporated to dryness to give the title compound (325 mg): IR 1726 cm−1 MS(TSP+ve) m/z 186 (M+MH4)+.

Provenance & Evidence