4-Hydroxymethylpyridine → HCID 9838340, compound

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Reaction Steps

To 4-pyridylcarbinol (1.2 g, 11.0 mmol) in THF (40 ml) at -18° C. was added n-butyllithium (2.5 M, 4.2 ml, 10.5 mmol) in hexane dropwise with stirring. After 10 minutes a solution of 1-adamantanecarbonyl chloride (2.0 g, 10.0 mmol) in THF (10 ml) was added and stirring continued at room temperature for 30 minutes. The mixture was poured into water, basified with saturated aqueous sodium bicarbonate, and extracted with ether. The ether extracts were combined, dried (Na2CO3) and concentrated, Chromatography, on elution with petrol-ether-triethylamine 100:50:1, gave the title compound (0.95 g, 35%), which crystallised from 60-80 petrol, m.p. 57°-58° C., IR νmax 1730 cm-1 ; 1H-NMR(CDCl3) δ1.74 and 1.96 (12H, 2s, adamantyl CH2), 2.05 (3H, s, adamantyl CH), 5.12 (2H, s, OCH2), 7.24 (2H, d, J 5.7 Hz, Py 3 and 6H), 8.60 (2H, d, J 5.7 Hz, Py 2 and 6H). Anal. Calcd: C, 75.24; H, 7.80; N, 5.16. Found: C, 75.34; H, 7.92; N, 5.04%.

Provenance & Evidence