反応 #491537

反応方程式

methyl 3-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzoate

S-Phos

tripotassium phosphate

DMF

→

T22.3

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

溶媒

water

water

反応条件

後処理

1. 1
   温度Before heating
2. 2
   workup.ADDITIONT22.2 (2.0 g, 9.5 mmol) was added
3. 3
   温度The resulting mixture was then cooled to room temperature
4. 4
   抽出extracted three times with EtOAc
5. 5
   乾燥After drying over anhydrous magnesium sulfate
6. 6
   ろ過filtering
7. 7
   その他the organic solvent was removed under reduced pressure
8. 8
   その他the product was then purified on silica gel (0-20% EtOAc in hexanes)

実験手順

A stirred solution of methyl 3-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzoate T3.2 (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, T22.2 (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 T22.3 as a colorless oil (2.50 g, 99% yield).

出典