HCID 68182046, compound → 2-{5-[(Oxan-2-yloxy)methyl]-1,2-oxazol-3-yl}but-3-yn-2-ol

Participants

Reaction Steps

To a solution of ethynylmagnesium bromide (2.93 mL of a0.5M solution in THF, 1.47 mmol) at 0° C. was slowly added 1-{5-[(oxan-2-yloxy)methyl]-1,2-oxazol-3-yl}ethanone (220 mg, 0.98 mmol) in THF (5 mL). The reaction mixture was allowed to warm to RT and stirred for 45 minutes. The reaction mixture was quenched with aqueous saturated NH4Cl solution (10 mL) and the organics were removed in vacuo. The product was extracted into EtOAc (20 ml×2) and the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Isolute column, 10-30% EtOAc in heptanes) to give the title product as a pale yellow oil: 1H NMR (250 MHz, CDCl3) delta 1.93-1.40 (9H, m), 2.66 (1H, s), 2.85 (1H, s), 3.69-3.46 (1H, m), 3.93-3.79 (1H, m), 4.94-4.54 (3H, m), 6.38 (1H, s); LC-MS: m/z=+251.95 (M+H)+.

Provenance & Evidence