Reaction Steps
(184) A solution of 2-(oxazol-5-yl)pyridine (97 mg, 0.66 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, 0.73 mmol, 0.29 mL), and stirred for 20 min. ZnCl2 (0.5 M in THF, 2.0 equiv, 1.32 mmol, 2.7 mL) was added at −75° C., and stirred for 45 min at 0° C. Cul (1.0 equiv, 0.66 mmol, 126 mg) was added, and the solution was stirred for 10 min at 0° C. A separate flask was charged with myristic acid (2 equiv, 1.32 mmol, 303 mg) in anhydrous CH2Cl2 (4.2 mL), and to this solution cooled to 0° C. under N2 was added oxalyl chloride (5 equiv, 6.6 mmol, 0.84 g, 0.58 mL). After stirring at rt for 2 h, the solution was concentrated under reduced pressure and dissolved in anhydrous THF (1.5 mL). The solution of myristoyl chloride 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)tetradecan-1-one (184) (102 mg, 0.29 mmol, 44% yield) as a white powder: mp 79-80° C.; 1H NMR (CDCl3, 250 MHz) d 8.65 (br d, J=4.8 Hz,1H), 7.89-7.75 (m, 3H), 7.34-7.25 (m,1H), 3.10 (t, J =7.3 Hz, 2H), 1.80-1.70 (m, 2H), 1.43-1.18 (m, 20H), 0.86 (br t, J=6.6 Hz, 3H); 13C NMR (CDCl3, 62.5 MHz) d 188.6, 157.4, 153.2, 150.1 (2C), 146.4, 137.1, 126.8, 124.1, 120.3, 39.1, 31.9, 29.6 (2C), 29.6, 29.4, 29.3 (2C), 29.2, 24.0, 22.7, 14.1; IR (KBr) umax 2960, 2878, 1705, 1598, 1426, 1387 cm31 1; MALDI-FTMS (DHB) m/z 357.2536 (C22H32N2O2+H+ requires 357.2536).
