2-Methyl-3-butyn-2-ol → HCID 56925648, compound

Participants

Reaction Steps

To a solution 2-methyl-3-butyn-2-ol (21) in acetonitrile (6 mL) was added DBU (0.80 mL, 6.61 mmol) at 0° C., then TFAA was added dropwise, also at 0° C. The reaction was stirred for 30 min. In another round bottom flask, DBU (0.80 mL, 6.61 mmol) was added to a solution of 2-bromo-5-hydroxy pyridine (1 g, 5.75 mmol) in 6 mL of acetonitrile at 0° C. Then 2-methyl-3-butyn-2-ol was added dropwise into this reaction, which was stirred for 30 additional min. The solvent was removed by rotary evaporation, and the residue was diluted with DCM. After separation, the organic layer was washed with 1M HCl, 1M NaOH, sat NaHCO3 and brine, was dried over MgSO4 and concentrated in vacuum. The crude product was dissolved in 2 ml of xylene and subjected to microwave irradiation (130° C., 220 W) for 30 min. The solvent was removed by rotary evaporation and the product concentrated in vacuum. The crude product was purified by column chromatography (silica gel) (10:1 Hx/EtOAc) to give 300 mg of a yellow solid (23% over the two steps). 1H NMR (CDCl3): 1.45 (s, 6H), 5.86 (d, 1H, J=10.4), 6.44 (d, 1H, J=10), 6.90 (d, 1H, J=8.8), 7.14 ppm (s, 1H, J=8.4). HRMS (ESI) m/z calcd for C10H11NOBr [(M+H)+] 240.0024. found: 240.0026.

Provenance & Evidence