反応 #7860

反応方程式

methyl 3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate

2-pyridylzinc bromide

→

methyl 3-methoxy-4-pyridin-2-ylbenzoate

溶媒

THF

反応条件

後処理

1. 1
   その他The mixture was degassed with argon for an additional 30 minutes
2. 2
   温度heated
3. 3
   温度at reflux under an argon atmosphere overnight
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The resultant brown residue was partitioned between EtOAc (1500 mL) and 50% saturated NaHCO3 (1000 mL)
6. 6
   抽出The aqueous layer was extracted with EtOAc (500 mL)
7. 7
   洗浄the combined organic layers washed with brine
8. 8
   乾燥dried over MgSO4
9. 9
   ろ過filtered
10. 10
    濃縮concentrated in vacuo
11. 11
    その他The crude product was purified by column chromatography (0–25% EtOAc/hexanes)

実験手順

To 300 mL of degassed THF was added methyl 3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate (20.95 g, 66.7 mmol), 2-pyridylzinc bromide (200 mL of 0.5M solution in THF, 100 mmol), and tetrakis(triphenylphosphine)palladium(0) (5.00 g, 4.3 mmol). The mixture was degassed with argon for an additional 30 minutes and heated at reflux under an argon atmosphere overnight. The reaction mixture was cooled to rt and concentrated in vacuo. The resultant brown residue was partitioned between EtOAc (1500 mL) and 50% saturated NaHCO3 (1000 mL). The aqueous layer was extracted with EtOAc (500 mL), and the combined organic layers washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (0–25% EtOAc/hexanes) to give methyl 3-methoxy-4-pyridin-2-ylbenzoate as a colorless solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.70 (d, 1H), 7.92–7.83 (m, 3H), 7.70–7.65 (m, 2H), 7.40–7.36 (m, 1H), 3.91 (s, 3H), 3.90 (s, 3H).

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