4-Bromopyridinium chloride → HCID 66799224, compound

Participants

Reaction Steps

1,4-Dioxaspiro[4.5]decan-8-ol (4.93 g, 31.202 mmol, 1.0 eq.) was dissolved in DMSO (100 ml); potassium tert-butylate (10.5 g, 93.61 mmol, 3.0 eq.) was added at 0° C. and the mixture was stirred for 1 hour at RT. 4-Bromopyridine HCl (9.1 g, 46.803 mmol, 1.5 eq.) was then added at 0° C. and stirring was carried out for 16 hours at RT. After monitoring by TLC, the reaction mixture was concentrated and the residue was taken up in water (200 ml) and extracted with DCM (2×200 ml). The combined org. phases were washed with water (200 ml) and sat. NaCl solution (250 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 40% ethyl acetate in hexane). Yield: 35% (2.6 g, 11.063 mmol)

Provenance & Evidence