Azobisisobutyronitrile → HCID 11249951, compound

In a typical procedure for reverse fluorous solid phase extraction in the studies of FIG. 4, a perfluoroalkyl iodide such as perfluorodecyl iodide (RfI, 323 mg, 0.5 mmol), allyltributyltin (330 mg, 1 mmol), AIBN (9 mg, 0.05 mmol) and hexane (5 ml) were placed in a flask under an argon atmosphere and the mixture was refluxed for 5 h. After removal of the volatile components by evaporation, the mixture was submitted to separation by reverse fluorous solid phase extraction. A short column was packed with regular silica gel (6.0 g) using FC-72/Et2O (2/1) as the solvent. The crude reaction mixture was then loaded onto this column and eluted with 20 ml of FC-72/Et2O (2/1) to give 3-(perfluorodecyl)prop-1-ene in 97% yield (271 mg). After similar reactions and separations, the allylated products 2a-d, 3a-d and 4a-d were isolated in yields ranging from 69-93%. The nuclear magnetic resonance (NMR) spectra of these products were clean, and gas chromatography (GC) or high pressure liquid chromatography (HPLC) purities exceeded 90% in all cases. The purity of the products was determined by GC in the case of R═H or R═Me and HPLC (Nova Pak® Silica, UV detection at 254 nm) in the case of R═Ph.

1. extractionIn a typical procedure for reverse fluorous solid phase extraction in the studies of FIG. 4
2. temperaturethe mixture was refluxed for 5 h
3. customAfter removal of the volatile components
4. customby evaporation
5. customthe mixture was submitted to separation by reverse fluorous solid phase extraction
6. customThe crude reaction mixture
7. washeluted with 20 ml of FC-72/Et2O (2/1)

ORD record

ord-62ecb49063c34ababe95f7a6e41f56b0

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07364908B2