Tetrabutylammonium Fluoride → N-[4-Chloro-3-(hydroxymethyl)benzyl]-N-methylacetamide

Participants

Reaction Steps

To a solution of N-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-chlorobenzyl]-N-methylacetamide from the previous step (1 eq.) in THF (0.8M) was added tetrabutylammonium fluoride (1.0 M THF solution, 1.5 eq.). The resulting reaction mixture was stirred at RT for 1 h. After quenching the reaction with 10% aq. HCl, the mixture was extracted with EtOAc. The combined organic extracts were washed with 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, 9:1 (v/v) CH2Cl2:MeOH) afforded the title compound as a light yellow oil.

Provenance & Evidence