Pyridine → HCID 54718313, compound

Participants

Reaction Steps

A solution of (adamantan-1-yloxy)-acetic acid (32.3 g, 153 mmol) and 1,1′-carbonyl-diimidazole (27.6 g, 170 mmol) in DCM (600 mL) was stirred at 0° C. for 15 minutes, then at room temperature for 75 minutes. The mixture was concentrated in vacuo (˜300 mL) and the solution was then added dropwise, over 20 minutes, to a solution of 2,2-dimethyl-1,3-dioxan-4,6-dione (22.1 g, 153 mmol) and pyridine (30 mL, 371 mmol) in DCM (450 mL) at 0° C. under argon. The mixture was allowed to warm to room temperature and stirred for 16 hours. The organic solution was washed with 2N HCl (2×500 mL), brine (500 mL) and dried (MgSO4). The filtrate was evaporated and the residue triturated with hexane to give the title compound as a white solid (50.1 g, 97%). 1H NMR (CDCl3) 4.91 (2H, s), 2.18 (3H, br s), 1.81-1.81 (6H, m), 1.73 (6H, s), 1.68-1.58 (6H, m).

Provenance & Evidence