4-Toluenesulfonyl chloride → 3-Hydroxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

3-tert-Butyldimethylsilyloxy-1H-pyridin-2-one (1 eq.) (Posner et al. J. Org. Chem. 1992, 57, 4088.) is cooled down to −78° C., in THF (10 mL) and is treated with n-BuLi (1.6 M soln. in hexane, 1.1 eq.). The solution is stirred for 20 min at −78° C., followed by the addition of p-toluenesulfonyl chloride (1.1 eq.). The solution is allowed to warm up to room temperature over one hr, quenched with water (10 mL), extracted with EtOAc (3×), washed with brine (1×), dried (Na2SO4) and concentrated. The residue is taken up in ethanol (10 mL) and treated with conc. HCl (2 mL). The mixture is allowed to stir for 1 h, the solvent is removed to obtain the desired compound as a white solid.

Provenance & Evidence