Tetrabutylammonium Fluoride → 2-Chloro-5-ethynylpyridine

2-Chloro-5-trimethylsilanylethynyl-pyridine (1.00 g, 4.77 mmol) was taken up in THF (23.8 ml) under argon at 0° C. Tetrabutylammonium fluoride (5.72 ml of 1.0 M in THF, 5.72 mmol) was added dropwise over 5 minutes. The mixture was then allowed to warm to room temperature and maintained at room temperature for 1.5 hours. The reaction was quenched with saturated aqueous ammonium chloride, and extracted three times with ethyl acetate. The organic fractions were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography (0-65% ethyl acetate/hexanes) to afford the title compound.

1. temperaturemaintained at room temperature for 1.5 hours
2. customThe reaction was quenched with saturated aqueous ammonium chloride
3. extractionextracted three times with ethyl acetate
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting crude product was purified by silica gel chromatography (0-65% ethyl acetate/hexanes)

ORD record

ord-0ea4ea62381b4707b1f2c1f149774f11

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2