Triacetoxyperiodinane → N-(4-Chloro-3-formylbenzyl)-N-methylacetamide

Participants

Reaction Steps

To a solution of N-[4-chloro-3-(hydroxymethyl)benzyl]-N-methylacetamide from the previous step (1 eq.) in CH2Cl2 (0.8 M) was added Dess-Martin periodinane (1.2 eq.) portionwise. The resulting suspension was stirred at RT for 3 h. The reaction was quenched with MeOH and H2O. The organic layer was separated and the aqueous layer was back-extracted with EtOAc. The combined organic extracts were washed sat. aq. NaHCO3 and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded a pale yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, EtOAc) afforded the title compound as a pale yellow oil.

Provenance & Evidence