Oxazole → Dimethyl 5-(oxazol-2-yl)isophthalate

Temperature

0 °C

To a stirred solution of oxazole ((0.28 mL, 4.2 mmol) in THF (10 mL) at −78° C. was added nBuLi (2.8 mL 1.6 N solution in hexane, 4.4 mmol). ZnCl2 (20 mL 0.5M soln, 10 mmol) was added after 30 min and the reaction mixture was warmed up to 0° C. for 1 h. To the resulting mixture was added dimethyl 5-iodoisophthalate (1.28 g, 4.0 mmol) and Pd(PPh3)4 and was heated at reflux for 5 h. The reaction mixture was cooled to room temperature and diluted with EtOAc and H2O. The layers were separated and the organic layer was washed with, brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (20% EtOAc in hexanes) to provide dimethyl 5-(oxazol-2-yl)isophthalate (568 mg, 54%).

1. temperaturewas heated
2. temperatureat reflux for 5 h
3. temperatureThe reaction mixture was cooled to room temperature
4. customThe layers were separated
5. washthe organic layer was washed with, brine
6. dry with materialdried with Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by column chromatography (20% EtOAc in hexanes)

ORD record

ord-c0a42131807d4676b485b615686e5698

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299267B2