Potassium bisulfate → 1-(2-Naphthylmethyl)-1H-imidazol-5-ylacetaldehyde

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (40.8 mg, 1.07 mmol) in tetrahydrofuran (5 ml) at -45° C. was added a solution of N-methoxy-N-methyl-1-(2-naphthylmethyl)-1H-imidazol-5-ylacetamide (243 mg, 0.895 mmol) in tetrahydrofuran (5 ml) via cannula at such a rate to maintain the temperature at <-35° C. After the addition was complete, the reaction was allowed to warm to +5° C. and then recooled to -35° C. To this solution was added a solution of potassium bisulfate (272 mg) in water (1 ml). The mixture was stirred for 30 min at room temperature and then filtered through celite. The celite pad was washed with ethyl acetate (25 ml). The combined filtrates were washed with sat. sodium bicarbonate (10 ml) and then water (10 ml). The organic layer was dried (MgSO4), filtered and evaporated in vacuo to give 30 as a clear oil. This material was used as is in the next step.

Provenance & Evidence