Tetrabutylammonium Fluoride → 3-((4-Ethynyl-1H-pyrazol-1-yl)methyl)-5-methylisoxazole

Participants

Reaction Steps

5-Methyl-3-((4-((trimethylsilyl)ethynyl)-1H-pyrazol-1-yl)methyl)isoxazole (31) (0.55 g, 2.12 mmol) was dissolved in 3 ml THF and stirred at RT. To the stirred solution was then added a 1M solution of TBAF in THF (3 ml, 3 mmol). After 10 minutes, the reaction was diluted with ethyl acetate (20 ml) and water (20 ml). The organic solution was collected, dried and concentrated. The crude product was purified on a short silica column eluting with 5% ethyl acetate in DCM. The pure fractions provided the title compound as a pale brown solid (278 mg, 70%). 1H-NMR (500 MHz, CDCl3) 2.38 (s, 3H), 3 (s, 1H), 5.29 (s, 2H), 5.9 (s, 1H), 7.61 (s, 1H), 7.63 (s, 1H).

Provenance & Evidence