Methane → 1,1,1-Trifluoro-2-trifluoromethyl-5-vinyloxy-pentan-2-ol

Temperature

100 °C

1,1,1-Trifluoro-2-trifluoromethyl-2,5-pentanediol (11.3 g, 50 mmol), toluene (50 mL), sodium carbonate (10.6 g,100 mmol), chloro-1,5-cyclooctadiene iridium(I) dimer (0.34 g, 0.5 mmol), vinyl acetate(14 mL, 150 mmol) were placed in a dry 250 mL round-bottom flask equipped with a stir bar, condenser, and nitrogen inlet. The reaction mixture was heated to 100° C. and stirred for 3 hours, after which time it was cooled to room temperature. Diethyl ether (50 mL) was added to quench the reaction. After adding charcoal, the mixture was stirred for 1 hr and filtered with Celite 521. Diethyl ether, excess vinyl acetate, and solvent were distilled off under reduced pressure. The degree of the transetherification of the primary diol was found to be 52% by GC. Vacuum distillation (68–70° C., 15 mm Hg) afforded 3.13 g (25%) of colorless liquid.

1. customequipped with a stir bar, condenser, and nitrogen inlet
2. temperatureafter which time it was cooled to room temperature
3. customto quench
4. customthe reaction
5. stirringthe mixture was stirred for 1 hr
6. filtrationfiltered with Celite 521
7. distillationDiethyl ether, excess vinyl acetate, and solvent were distilled off under reduced pressure
8. distillationVacuum distillation (68–70° C., 15 mm Hg)

ORD record

ord-7f12955a3c724ce2aefa3d1187567335

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07150957B2