Oxalyl chloride → HCID 68544735, compound

Participants

Reaction Conditions

Reaction Steps

(163) A solution of 2-(oxazol-4-yl)pyridine (4 mg, 0.027 mmol) in anhydrous THF (1 mL) cooled to −75° C. under N2 was treated with n-BuLi (2.5 M in hexanes, 1.1 equiv, 0;030 mmol, 12 mL), and stirred for 20 min. ZnCl2 (0.5 M in THF, 2.0 equiv, 0.054 mmol, 22 mL) was added at −75° C., and stirred for 45 min at 0° C. Cul (1.0 equiv, 0.027 mmol, 5 mg) was added, and the solution was stirred for 10 min at 0° C. A separate flask was charged with oleic acid (2 equiv, 0.054 mmol, 15 mg) in anhydrous CH2Cl2 (0.5 mL), and to this solution cooled to 0° C. under N2 was added oxalyl chloride (5 equiv, 0.27 mmol, 34 mg, 24 mL). After stirring at rt for 2 h, the solution was concentrated under reduced pressure and dissolved in anhydrous THF (0.5 mL). The solution of oleoyl 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, 1.5 cm×17.5 cm, 2% MeOH—CH2Cl2) afforded 1-(4-(pyridin-2-yl)oxazol-2-yl)octadec-9-en-1-one (163) (5 mg, 0.011 mmol, 42% yield) as a brown residue: 1H NMR (CDCl3, 250 MHz) d 8.66 (br d, J=4.8 Hz,1H), 7.90-7.68 (m, 4H), 5.40-5.25 (m, 2H), 3.10 (t, J=7.4 Hz, 2H), 2.10-1.93 (m, 4H), 1.80-1.72 (m, 2H), 1.47-1.17 (m, 20H), 0.86 (br t, J=6.6 Hz, 3H); IR (CDCl3) umax 2925, 2860, 1705, 1605, 1570, 1501, 1425, 1385 cm−1; MALDI-FTMS (DHB) m/z 411.3003 (C26H38N2O2+H+ requires 411.3006).

Provenance & Evidence