Oxalyl chloride → HCID 68547196, compound

Participants

Reaction Conditions

Reaction Steps

(164) A solution of 3-(oxazol-4-yl)pyridine (6 mg, 0.041 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, 0.045 mmol, 18 mL), and stirred for 20 min. ZnCl2 (0.5 M in THF, 2.0 equiv, 0.082 mmol, 33 mL) was added at −75° C., and stirred for 45 min at 0C. Cul (1.0 equiv, 0.041 mmol, 8 mg) was added, and the solution was stirred for 10 min at 0° C. A separate flask was charged with oleic acid (2 equiv, 0.082 mmol, 23 mg) in anhydrous CH2Cl2 (0.5 mL), and to this solution cooled to 0° C. under N2 was added oxalyl chloride (5 equiv, 0.41 mmol, 52 mg, 37 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-3-yl)oxazol-2-yl)octadec-9-en-1-one (164) (4 mg, 0.009 mmol, 23% yield) as a brown residue: 1H NMR (CDCl3, 250 MHz) d 8.99 (br s, 1H), 8.65 (br d, J=4.7 Hz, 1H), 8.04 (br d, J=7.5 Hz, 1H), 7.86-7.54 (m, 2H), 5.41-5.26 (m, 2H), 3.10 (t, J=7.4 Hz, 2H), 2.10-1.93 (m, 4H), 1.83-1.70 (m, 2H), 1.45-1.20 (m, 20H), 0.86 (br t, J=6.6 Hz, 3H); IR (CDCl3) umax 2926, 2871, 1700, 1601, 1564, 1510, 1421, 1382 cm−1; MALDI-FTMS (DHB) m/z 411.3012 (C26H38N2O2+H+ requires 411.3006).

Provenance & Evidence