反応 #491538

反応方程式

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

S-Phos

tripotassium phosphate

DMF

water

→

T23.1

Methyl 3-(2-methyl-1-propenyl)-4-(tetrahydro-2H-pyran-2-yloxy)benzoate

反応条件

後処理

1. 1
   その他The mixture was purged with nitrogen
2. 2
   温度Before heating
3. 3
   workup.ADDITIOND3007G1) was added
4. 4
   workup.STIRRINGstirred for 23 hours
5. 5
   温度The mixture was then cooled to room temperature
6. 6
   workup.ADDITIONdiluted with brine
7. 7
   抽出extracted three times with EtOAc
8. 8
   乾燥After drying over anhydrous magnesium sulfate
9. 9
   ろ過filtering
10. 10
    その他the organic solvent was removed under reduced pressure
11. 11
    その他the product was then purified on silica gel (0-10% EtOAc in hexanes)

実験手順

A mixture of methyl 3-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzoate T3.2 (0.500 g, 1.6 mmol), palladium acetate (0.036 g, 0.16 mmol), S-Phos (0.13 g, 0.32 mmol) and tripotassium phosphate (0.32 mL, 4.0 mmol) in DMF (10.00 mL, 129 mmol) and water (0.40 mL, 22 mmol) was stirred. The mixture was purged with nitrogen and placed under vacuum and the process repeated three times. Before heating, 2-methylprop-1-enylboronic acid (0.24 g, 2.4 mmol, commercially available from Synthonix, Cat. No. D3007G1) was added, and the mixture was heated to 70° C. and stirred for 23 hours. The mixture was then cooled to room temperature, diluted with brine, 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 (0-10% EtOAc in hexanes) to yield T23.1 as a colorless oil (0.460 g, 100% yield).

出典