Ethylene Oxide → 2-Fluoro-4-(3-hydroxypropyl)pyridine

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Reaction Steps

This compound was prepared, starting from compound 41 (7.00 g, 6.30 mmol) and ethylene oxide (4.20 mL, 84.1 mmol), according to the procedure developed for compound 42. The purification was performed using colomm chromatography (SiO2, AcOEt/pentane, 6/4, v/v) to give alcohol 48 (5.16 g, 33.3 mmol) as a yellow oil. Yield 53%; Rf (SiO2, AcOEt/pentane 6/4, v/v) 0.52; IR (CCl4) ν 1412, 1613, 2939, 3639 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.84 (m, 2H), 2.72 (t, 2H, J=7.4 Hz), 3.14 (se, 1H), 3.62 (t, 2H, J=6.2 Hz), 6.72 (s, 1H), 6.98 (m, 1H), 8.01 (d, 1H, J=5.1 Hz); MS m/z 155 (M+, 6), 137 (25), 124 (12), 111 (100), 91 (21), 77 (14), 57 (14), 51 (16).

Provenance & Evidence