2-(Pyridin-2-yl)oxazole → 7-Phenyl-1-(2-(pyridin-2-yl)oxazol-5-yl)-heptan-1-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(pyridin-2-yl)-oxazole (S1, 54 mg, 0.369 mmol) in THF (2 mL) was cooled to −78° C. before it was treated dropwise with 2.5 M n-BuLi (0.177 mL, 0.443 mmol). The reaction mixture was stirred at −78° C. for 20 min before 7-phenylheptanal (77 mg, 0.405 mmol) in THF (1 mL) was added dropwise. The solution was stirred for an additional 10 min at −78° C. before being warmed to room temperature. The reaction mixture was quenched with the addition of saturated aqueous NaHCO3, diluted with EtOAc and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4 and the solvent was removed under reduced pressure. Flash chromatography (SiO2, 20-70% EtOAc-hexanes) yielded the title compound (35 mg, 28%) as a colorless oil: 1H NMR (CDCl3, 500 MHz) δ 8.77 (s, 1H), 8.17 (d, 1H, J=8.0 Hz), 7.86 (t, 1H, J=8.0 Hz), 7.41 (m, 1H), 7.35-7.32 (m, 2H), 7.23 (m, 3H), 7.18 (s, 1H), 4.93 (t, 1H, J=6.5 Hz), 3.22 (br s, 1H), 2.65 (t, 2H, J=6.5 Hz), 2.01-1.98 (m, 2H), 1.68-1.66 (m, 2H), 1.44-1.42 (m, 5H); 13C NMR (CDCl3, 125 MHz) δ 160.3, 156.1, 150.2, 146.4, 143.1, 137.5, 128.8, 128.6, 126.0, 125.1, 124.9, 122.5, 66.5, 36.3, 35.8, 31.8, 29.6 (2C), 25.8.

Provenance & Evidence