Sodium Hydroxide → HCID 58047468, compound

To a solution of 5-ethoxy-2-[(trimethylsilyl)ethynyl]pyridine (2.74 g) in methanol (40 mL) was added 8M aqueous sodium hydroxide solution (3.73 mL) 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 pale-brown powder (1.72 g).

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-83a8e0173ba2432fb5fb02f19bfdabd9

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729102B2