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

温度

70 °C

A stirred solution of methyl 3-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzoate 66.6F (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, 66.18B (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 66.18C 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レコード

ord-4df76575711f4b7f9a3a5b2cdc8a1910

出典データセット

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08030354B2