Reaction Steps
(187) A solution of 2-(oxazol-5-yl)pyridine (100 mg, 0.68 mmol) in anhydrous THF (5 mL) cooled to −75° C. under N2 was treated with n-BuLi (2.5 M in hexanes, 1.1 equiv, 0.75 mmol, 0.30 mL), and stirred for 20 min. ZnCl2 (0.5 M in THF, 2.0 equiv, 1.40 mmol, 2.8 mL) was added at −75° C., and stirred for 45 min at 0° C. Cul (1.0 equiv, 0.68 mmol, 130 mg) was added, and the solution was stirred for 10 min at 0° C. Decanoyl chloride (2 equiv, 1.4 mmol, 270 mg, 0.29 mL) was added and the solution was stirred for 1 h at 0° C. The reaction was diluted with EtOAc (10 mL), and washed with 15% aqueous NH4OH (1×10 mL), H2O (1×10 mL), and saturated aqueous NaCl (1×10 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. Flash chromatography (SiO2, 2.5 cm×17.5 cm, 20% EtOAc-hexanes) afforded 1-(5-(pyridin-2-yl)oxazol-2-yl)decan-1-one (187) (80 mg, 0.27 mmol, 40% yield) as a light brown powder: mp 56-57° C.; 1H NMR (CDCl3, 250 MHz) d 8.69-8.62 (m, 1H), 7.87-7.75 (m, 3H), 7.33-7.25 (m, 1H), 3.08 (t, J=7.7 Hz, 2H), 1.81-1.69 (m, 2H), 1.41-1.19 (m, 12H), 0.86 (br t, J=7.0 Hz, 3H); 13C NMR (CDCl3, 62.5 MHz) d 188.5, 157.3, 153.1, 150.0, 146.2, 136.9, 127.8, 124.1, 120.3, 39.1, 31.8, 29.4, 29.3, 29.2, 29.1, 24.0, 22.6, 14.0; IR (KBr) umax 2930, 2845, 1697, 1601, 1422, 1380 cm−1; MALDI-FTMS (DHB) m/z300.1911 (C18H24N2O2+H+ requires 301.1910).
