Pyridine → HCID 11085130, compound

Participants

Reaction Steps

Pyridine (4.74 g, 60 mmol) and tert-butyldimethylsilyl chloride (4.83 g, 32 mmol) were added to a solution of cyclohex-2-enol (1.96 g, 20 mmol) in DCM (40 mL). The reaction mixture was stirred at RT overnight. The mixture was concentrated and the residue was dispersed in EtOAc and water. The organic phase was separated and washed with brine, dried over anhydrous Na2SO4, concentrated, and purified by silica flash chromatography eluting with EtOAc and petroleum ether (5-10% EtOAc) to give the title compound as an oil (4.1 g, 97%). 1H NMR (400 MHz, CDCl3) δ ppm 0.06-0.09 (m, 6H), 0.92 (s, 9H), 1.50-1.57 (m, 2H), 1.74-1.89 (m, 2H), 1.93-2.03 (m, 2H), 4.21-4.23 (m, 1H), 5.61-5.64 (m, 1H), 5.72-5.76 (m, 1H).

Provenance & Evidence