Pyridine → HCID 22390864, compound

To a 0° C. solution of triphenylphosphine (2.07 g, 7.90 mmol) in methylene chloride (20 mL) was added bromine (0.4 mL, 7.90 mmol) dropwise. To the resulting cloudy mixture was added a solution of 3-benzofuran-3-yl-propan-1-ol (1.16 g, 6.58 mmol) and pyridine (1.07 mL, 13.2 mmol) in methylene chloride (10 mL). The reaction was stirred at room temperature for 4 hours, then was diluted with diethyl ether (100 mL) and filtered. The ethereal solution was washed with 1 M aqueous potassium hydrogen sulfate (50 mL), then with saturated aqueous sodium bicarbonate (50 mL), and finally with brine (50 mL), then was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuum. Flash chromatography on SiO2 (CH2Cl2) afforded 1.5 g (96%) of the title compound: 1H NMR (CDCl3, 400 MHz) δ 7.56 (d, J=7.8 Hz, 1 H), 7.47 (d, J=8.1 Hz, 1 H), 7.46 (s, 1 H), 7.7.22-7.35 (m, 2 H), 3.45 (t, J=6.4 Hz, 2 H), 2.87 (t, J=7.1 Hz, 2 H), 2.25 (quint, J=7.2 Hz, 2 H).

1. filtrationfiltered
2. washThe ethereal solution was washed with 1 M aqueous potassium hydrogen sulfate (50 mL)
3. dry with materialwith saturated aqueous sodium bicarbonate (50 mL), and finally with brine (50 mL), then was dried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuum

ORD record

ord-5f9cefb7224441738374752ba593bbd9

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06800637B2