Dimethylformamide → Methyl 3-(1-(1,1-dimethylethyl)ethenyl)-4-(tetrahydro-2H-pyran-2-yloxy)benzoate

Temperatur

70 °C

A stirred solution of methyl 3-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzoate T6.6 (2.50 g, 7.9 mmol), palladium acetate (0.18 g, 0.79 mmol), S-Phos (0.65 g, 1.6 mmol), tripotassium phosphate (1.6 mL, 20 mmol) in DMF (15.00 mL, 194 mmol) and water (0.600 mL, 33 mmol) was purged 3 times with nitrogen and placed under vacuum and the process repeated three times. Before heating, T12.2 (2.0 g, 9.5 mmol) was added, and the mixture was heated to 70° C. and stirred for 19 hours. The resulting mixture was then cooled to room temperature, diluted with water and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-20% EtOAc in hexanes) to yield T12.3 as a colorless oil (2.50 g, 99% yield).

1. temperatureBefore heating
2. temperatureThe resulting mixture was then cooled to room temperature
3. extractionextracted three times with EtOAc
4. dry with materialAfter drying over anhydrous magnesium sulfate
5. filtrationfiltering
6. customthe organic solvent was removed under reduced pressure
7. customthe product was then purified on silica gel (0-20% EtOAc in hexanes)

ORD-Eintrag

ord-1a0b1447959f41859f4b748537e45924

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08450522B2