Tetrabutylammonium Fluoride → 2-(4-Ethynyl-1H-pyrazol-1-yl)-N,N-dimethylacetamide

Participants

Reaction Steps

N,N-Dimethyl-2-(4-((trimethylsilyl)ethynyl)-1H-pyrazol-1-yl)acetamide (Preparation 100, 0.55 g, 2.2 mmol) was dissolved in dry THF (10 ml). To the stirred solution was then added a solution of TBAF in THF (2.4 ml of a 1M solution in THF, 2.4 mmol). After 20 minutes the reaction was concentrated in vacuo and the residue taken up in ethyl acetate. The organic solution was washed with water, brine and dried over sodium sulphate. The organic solution was then concentrated in vacuum and the crude product purified by silica gel column chromatography eluting with neat ethyl acetate to afford the title compound as a pale brown powder (0.3 g, 77%). 1H-NMR (500 MHz, CDCl3): δ 2.98 (s, 3H), 3.01 (s, 1H), 3.07 (s, 3H), 4.95 (s, 2H), 7.62 (s, 1H), 7.69 (s, 1H).

Provenance & Evidence