반응 #7860

반응 방정식

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

2-pyridylzinc bromide

→

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

용매

THF

반응 조건

후처리

1. 1
   기타The mixture was degassed with argon for an additional 30 minutes
2. 2
   온도heated
3. 3
   온도at reflux under an argon atmosphere overnight
4. 4
   농축concentrated in vacuo
5. 5
   기타The resultant brown residue was partitioned between EtOAc (1500 mL) and 50% saturated NaHCO3 (1000 mL)
6. 6
   추출The aqueous layer was extracted with EtOAc (500 mL)
7. 7
   세척the combined organic layers washed with brine
8. 8
   건조dried over MgSO4
9. 9
   여과filtered
10. 10
    농축concentrated in vacuo
11. 11
    기타The crude product was purified by column chromatography (0–25% EtOAc/hexanes)

실험 절차

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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