Diisobutylaluminum hydride → 2-(4,6-Dichloro-pyrimidin-5-yl)-propan-1-ol

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Reaction Steps

To a solution of 2-(4,6-Dichloro-pyrimidin-5-yl)-propionic acid methyl ester (0.5 g, 2.13 mmol) in ether (40 mL) at −78° C. was added DIBAL-H (1.5M, 4 mL, 6.0 mmol) dropwise. The mixture was allowed to warm up to room temperature and stirred for 3 hours. Then quenched with 2N HCl (10 mL) at −78° C. The aqueous phase was extracted with ethyl acetate (3×50 mL). The organic phase was dried and concentrated. The residue was subject to column chromatography, eluted by hexane/ethyl acetate (4:1) to give 2-(4,6-Dichloro-pyrimidin-5-yl)-propan-1-ol (0.40 g, 91%). 1H NMR (CDCl3, 400 MHz) δ 8.62 (s, 1H), 4.16 (m, 1H), 3.90 (m, 2H), 1.93 (s, 1H), 1.40 (d, J=7.2 Hz, 3H).

Provenance & Evidence