3-Hydroxypyridine → HCID 54469224, compound

Participants

Reaction Steps

To a solution of 11.9 g (0.125 mol) of 3-hydroxypyridine in 50 mL of DMSO at 15° C. was added 120 mL (0.12 mol) of a 1.0 M solution of sodium hexamethyldisilylazide in THF. After the reaction mixture was allowed to stir for 5 min, 25.9 g (0.10 mol) of (2S)-glycidyl 3-nitrobenzene sulfonate was added in one portion. The mixture was cooled with a room temperature water bath for 30 min. It s was then quenched by the addition of 250 mL of water and extracted with three portions of ethyl acetate. The combined aqueous extracts were washed sequentially with water and brine, dried over sodium sulfate, treated with granular charcoal, filtered and concentrated to give 7.7 g (51%) of an orange oil which was used without further purification. An analytical sample was prepared by flash chromatography (silica gel, 80% ethyl acetate/hexane): 1H NMR (400 MHz, CDCl3) a 8.31 (m, 1H), 8.21 (m, 1H), 7.20-7.22 (m, 2H), 4.29 (dd, 1H, J=1,6 Hz), 3.95 (m, 1H), 3.34 (m, 1H), 2.90 (t, 1H, J=3Hz), 2.75 (m, 1H).

Provenance & Evidence