Diisobutylaluminum hydride → 2-(4,6-Dichloropyrimidin-5-yl)ethan-1-ol

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Reaction Steps

To a solution of (4,6-Dichloro-pyrimidin-5-yl)-acetic acid methyl ester (0.52 g, 2.35 mmol) in ether (40 mL) at −78° C. was added DIBAL-H (1.5M, 4 mL, 6.05 mmol) dropwise. After addition, 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. Extracted with ethyl acetate (3×50 mL). The organic phase was dried and concentrated to give fairly pure 2-(4,6-Dichloro-pyrimidin-5-yl)-ethanol (0.44 g, 97%). 1H NMR (CDCl3, 400 MHz) δ 8.66 (s, 1H), 3.96 (t, J=6.8 Hz, 2H), 3.23 (t, J=6.8 Hz, 2H). 1.65 (s, 1H). MS (APCI+) [M+H]+194.

Provenance & Evidence