Water → 5-Benzyloxy-2-n-propylpyridine

Participants

Reaction Steps

5-Hydroxy-2-n-propylpyridine (13.72 g, 100 mmol) was dissolved in 200 ml of dry tetrahydrofuran under a nitrogen atmosphere, and at 0° C., 60% sodium hydride (7.0 g, 175 mmol) was added in small portions. The reaction mixture was stirred for 1/2 hour when a precipitate became visible. This precipitate was redissolved by adding 30 ml of dimethyl sulfoxide. Benzylbromide (13.1 ml, 18.84 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 3 hours. Water (200 mol) and 20 ml of triethylamine was added and The pH was adjusted to 12 with a saturated sodium hydrogen carbonate solution. The organic material was extracted into ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, and the solvent was evaporated. The crude product was purified by destillation and gave 19.39 g (85%) of 5-benzyloxy-2-n-propylpyridine as an orange coloured oil. B.p. 160-170° C. 0.3 mbar. MS(SP): m/z 227 (m+). 1H-NMR (CDCl3, 200 MHz) δ: 0.95 (t, 3H); 1.72 (sext, 2H); 2.70 (t, 2H); 5.05 (s, 2H); 7.02 (d, 1H); 7.18 (dd, 1H); 7.24-7.46 (m, 5H); 8.30 (d, 1H).

Provenance & Evidence