Butyryl chloride → HCID 11333397, compound

(193) A solution of 2-(oxazol-5-yl)pyridine (98 mg, 0.67 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, 0.74 mmol, 0.3 mL), and stirred for 20 min. ZnCl2 (0.5 M in THF, 2.0 equiv, 1.34 mmol, 2.7 mL) was added at −75° C., and stirred for 45 min at 0° C. Cul (1.0 equiv, 0.67 mmol, 128 mg) was added, and the solution was stirred for 10 min at 0° C. Butyryl chloride (2.0 equiv, 1.34 mmol, 143 mg, 0.14 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)butan-1-one (193) (68 mg, 0.31 mmol, 46% yield) as a light brown powder: mp 54-55° C; 1H NMR (CDCl3, 250 MHz) d 8.65-8.62 (m, 1H), 7.85-7.78 (m, 3H), 7.31-7.26 (m, 1H), 3.07 (t, J=7.3 Hz, 2H), 1.87-1.72 (m, 2H), 1.00 (t, J=7.7 Hz, 3H); 13C NMR (CDCl3, 62.5 MHz)d 188.4, 162.0, 157.3, 150.1, 146.3, 136.9, 126.8, 124.1, 120.3, 40.9, 17.5, 13.5; IR (KBr) umax 2963, 2933, 2872, 1675, 1469, 1426, 1387, 1227 cm−1; MALDI-FTMS (DHB) m/z 217.0968 (C12H12N2O2+H+ requires 217.0971).

1. stirringstirred for 45 min at 0° C
2. additionCul (1.0 equiv, 0.67 mmol, 128 mg) was added
3. stirringthe solution was stirred for 10 min at 0° C
4. stirringthe solution was stirred for 1 h at 0° C
5. washwashed with 15% aqueous NH4OH (1×10 mL), H2O (1×10 mL), and saturated aqueous NaCl (1×10 mL)
6. dry with materialThe organic layer was dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-0d7301ae476d4df48277bfadb86e0008

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662971B2