Aluminium lithium hydride → 2-(3-Chloropyridin-2-yl)propan-1-ol

To a −15° C. solution of the product of Example 38B (1.34 g, 6.27 mmol) in tetrahydrofuran (25 mL) was added lithium aluminum hydride (0.238 g, 6.27 mmol). The reaction mixture was kept between −5° C. and −15° C. for 1 hour and then quenched by the addition of solid sodium sulfate decahydrate. The quenched reaction mixture was filtered through a pad of celite with ethyl acetate and the filtrate concentrated. The residue was chromatographed on silica gel with 35% ethyl acetate-hexane to give the title compound (0.90 g, 84%). 1H NMR (300 MHz, DMSO-d6) δ ppm8.49 (dd, J=1.5, 4.6, 1H), 7.85 (dd, J=1.6, 8.1, 1H), 7.26 (dd, J=4.6, 8.1, 1H), 4.70-4.55 (m, 1H), 3.82-3.62 (m, 1H), 3.59-3.39 (m, 2H), 1.16 (d, J=6.5, 3H). MS (DCI) m/z 172 (M+H)+.

1. customquenched by the addition of solid sodium sulfate decahydrate
2. customThe quenched reaction mixture
3. filtrationwas filtered through a pad of celite with ethyl acetate
4. concentrationthe filtrate concentrated
5. customThe residue was chromatographed on silica gel with 35% ethyl acetate-hexane

ORD record

ord-263f327c60c645f0932e4429a371277a

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084616B2