Selectfluor → (S)-ethyl 2-tert-butoxy-2-(6-chloro-4-fluoro-1-hydroxy-3-methylnaphthalen-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-ethyl 2-tert-butoxy-2-(6-chloro-1-hydroxy-3-methylnaphthalen-2-yl)acetate (0.9705 g, 2.77 mmol) in anhydrous acetonitrile (20 mL) at 0° C. was added SelectFluor (1.078 g, 3.04 mmol) in one portion. The reaction mixture was stirred for 4 hours at 0° C., then 1 hour at room temperature. The reaction mixture was quenched with saturated Na2HPO4 solution and stirred for 20 minutes. The mixture was extracted with ethyl acetate (2×), dried (MgSO4), filtered, concentrated and stored overnight in a freezer. The residue was purified by flash column chromatography (silica gel, 0 to 15% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C19H21ClFO4: 367.8. Found: 366.9, 368.9.

Provenance & Evidence