Dichloromethane → 4-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-YL]benzaldehyde

A solution of methylene chloride (10.4 mL) was cooled to −78° C. To this was added dimethyl sulfoxide (416 uL) and oxalyl chloride (340 uL) and the solution was stirred for 5 minutes. {4-[5-(4-Isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-phenyl}-methanol (574 mg, 1.86 mmol) and diisopropyl ethyl amine (2.7 mL) were added to the reaction mixture and stirred at −78° C. for 30 minutes. The reaction mixture was warmed to room temperature, concentrated in vacuo and diluted with ethyl acetate. The mixture was washed with 1N HCl, saturated aqueous sodium bicarbonate and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to provide a crude residue. This residue was slurried in hexanes (10 mL) and heated to reflux. The solution was allowed to cool to ambient temperature and the resulting slurry was stirred for 1 hour and filtered. The solid was washed with minimal cold hexanes and dried in vacuo to give the title compound (183 mg, 32% yield) as a solid.

1. stirringstirred at −78° C. for 30 minutes
2. concentrationconcentrated in vacuo
3. additiondiluted with ethyl acetate
4. washThe mixture was washed with 1N HCl, saturated aqueous sodium bicarbonate and brine
5. dry with materialThe organic layer was dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto provide a crude residue
9. temperatureheated to reflux
10. temperatureto cool to ambient temperature
11. stirringthe resulting slurry was stirred for 1 hour
12. filtrationfiltered
13. washThe solid was washed with minimal cold hexanes
14. customdried in vacuo

ORD record

ord-4b465ebe46f545fe8f5efd58561a695b

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07671043B2