tert-Butyl acetate → Tert-butyl 2-(6-methylpyridin-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl acetate (1.013 mL, 7.50 mmol), 2-chloro-6-methylpyridine (638 mg, 5 mmol), chloro(2-di-t-butylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) (34.3 mg, 0.050 mmol) in Toluene (10 mL) at 0° C. in a 100-mL round bottom flask under N2 was added a solution of LHMDS (1M in toluene) (15.00 mL, 15.00 mmol) pre-cooled to 0° C. The reaction was stirred for 30 minutes. LCMS indicated the reaction was complete, so it was poured into ammonium chloride (aqueous, saturated) and water (1:1, 40 mL), and extracted with ethyl acetate (3×100 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0-25% EtOAc in hexanes) to afford 1,1-dimethylethyl (6-methyl-2-pyridinyl)acetate (918 mg, 4.43 mmol, 89% yield) as a yellow oil. LC-MS (ES) m/z=208 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41 (s, 9H), 2.44 (s, 3H), 3.68 (s, 1H), 7.12 (t, J=7.33 Hz, 2H), 7.64 (t, J=7.71 Hz, 1H).

Provenance & Evidence