Pyridine → Benzofuran-6-YL trifluoromethanesulfonate

HRID 869865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869865
[O:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.N1C=CC=CC=1.[O:17](S(C(F)(F)F)(=O)=O)[S:18]([C:21]([F:24])([F:23])[F:22])(=O)=[O:19]>ClCCl.O>[F:22][C:21]([F:24])([F:23])[S:18]([O:10][C:7]1[CH:8]=[CH:9][C:4]2[CH:3]=[CH:2][O:1][C:5]=2[CH:6]=1)(=[O:19])=[O:17]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1288446-Hydroxybenzofuran

Produkt 1

HCID 11357589Benzofuran-6-YL trifluoromethanesulfonateAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of benzofuran-6-ol (17.0 g, 127 mmol) in pyridine (20 g, 254 mmol) and dichloromethane (200 mL) was added Tf2O (53.7 g, 190 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to afford a crude product that was purified by column chromatography on silica gel (5-10% ethyl acetate in petroleum ether) to afford benzofuran-6-yl trifluoromethanesulfonate (30.0 g, 88.0% yield). 1H NMR (300 MHz, CDCl3) δ: 7.72 (d, J=2.1, 1H), 7.67 (d, J=8.7, 1H), 7.48 (d, J=1.5, 1H), 7.19 (dd, J=8.7, 2.1, 1H), 6.82-6.91 (m, 1H).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a crude product that
  7. customwas purified by column chromatography on silica gel (5-10% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-af78f512aeda49818bd7f5d2a3e725b1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969386B2

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