2,6-Di-tert-butylpyridine → HCID 90408960, compound

Participants

Reaction Steps

A mixture of 96C [1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-ol] (63 mg, 0.213 mmol), methyl 4-bromocrotonate (0.075 mL, 0.64 mmol), 2,6-di-tert-butylpyridine (0.334 mL, 1.49 mmol), and AgOTf (164 mg, 0.64 mmol) in DCM (0.5 mL) was stirred at rt in the dark for 3 days. LC-MS showed the presence of the product, and the reaction was filtered. The filtrate was concentrated in vacuo. The crude product was chromatographed [SiO2; continuous gradient of EtOAc/hexane (0% to 10% over 10 min)] to give the title compound (42 mg, 0.106 mmol, 50% yield) as an oil. 1H NMR (CDCl3) δ: 7.28-7.17 (m, 3H), 7.07-6.98 (m, 3H), 6.94-6.86 (m, 3H), 6.78 (ddd, J=8.1, 2.4, 1.0 Hz, 1H), 6.02 (dt, J=15.6, 2.2 Hz, 1H), 4.07 (dd, J=4.2, 2.1 Hz, 2H), 3.84 (t, J=1.4 Hz, 2H), 3.67 (s, 3H), 2.11-2.03 (m, 4H), 1.97-1.88 (m, 2H), 1.86-1.77 (m, 2H).

Provenance & Evidence