Acetic Acid → 2-(5-Bromopyridin-2-yl)ethan-1-ol

To a solution of (5-bromopyridin-2-yl)acetic acid (60.0 mg, 0.278 mmol) in dry tetrahydrofuran (1.4 mL) was added dropwise borane-tetrahydrofuran complex (1.06M in tetrahydrofuran, 0.34 mL, 0.361 mmol) under N2. The mixture was stirred at room temperature for 19 hours and water (5 mL)-acetic acid (5 mL) was added slowly. The mixture was concentrated under reduced pressure, the residue was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3→ethyl acetate) to give the title compound as a yellow oil (45 mg, yield 80%).

1. concentrationThe mixture was concentrated under reduced pressure
2. additionthe residue was poured into saturated aqueous sodium hydrogen carbonate solution
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3→ethyl acetate)

ORD record

ord-9db866ea11c94adb9508a299b77939a7

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536176B2