Tetrabutylammonium Fluoride → 5-(Cyclopropylmethoxy)-2-ethynylpyridine

To a solution of 5-(cyclopropylmethoxy)-2-[(trimethylsilyl)ethynyl]pyridine (773 mg) in THF (15 mL) was added a THF solution (1.0 M, 4.1 mL) of tetrabutylammonium fluoride at room temperature, and the reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate and water, and the aqueous layer was separated from the organic layer. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a colorless oil (591 mg).

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionThe residue was diluted with ethyl acetate and water
3. customthe aqueous layer was separated from the organic layer
4. extractionThe separated aqueous layer was extracted again with ethyl acetate
5. washThe combined organic layer was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-117be9943f804f5f9e5adf491693a5e3

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729102B2