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-916deb0365bf4401a69e629fbff88db9

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947425B2