HCID 44818468, compound → 4-Pyridinylacetone

Participants

Reaction Conditions

Reaction Steps

To a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of argon, was added THF (70 mL) and N-methoxy-N-methyl-2-(pyridin-4-yl)acetamide (7.0 g, 0.039 mol, 1.0 equiv). The mixture was cooled to 0° C. and CH3MgBr (3M in THF, 65 mL, 5.0 equiv) was added dropwise. The resulting solution was warmed to ambient temperature and stirred for 16 h. The reaction mixture was cooled to 0° C. and quenched by the addition of saturated NH4Cl (aq, 100 mL). The resulting solution was extracted with EtOAc (3×200 mL). The organic layers were combined, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified by flash chromatography (silica gel, CH2Cl2/CH3OH (20:1)) to yield 2.7 g (51%) of the title compound as yellow oil. 1H-NMR (400 MHz, CDCl3): δ ppm 8.58 (m, 2H), 7.17 (d, J=0.4 Hz, 2H), 3.75 (s, 2H), 2.24 (s, 3H).

Provenance & Evidence