Imidazole → 3-(2-Iodoethyl)-6-methoxy-1-benzofuran

HRID 1767996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767996
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7]([CH2:10][CH2:11]O)=[CH:8][O:9][C:5]=2[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:34]I.N1C=CN=C1>C1COCC1>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7]([CH2:10][CH2:11][I:34])=[CH:8][O:9][C:5]=2[CH:4]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 236144442-(6-Methoxy-benzofuran-3-yl)ethanol

Produkt 1

HCID 236144453-(2-Iodoethyl)-6-methoxy-1-benzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(6-methoxy-1-benzofuran-3-yl)ethanol (960 mg, 5 mmol) in anhydrous THF (50 ml), triphenylphosphine (1.572 g, 6 mmol), iodine (1.518 g, 6 mmol) and imidazole (408 mg, 6 mmol) were added at room temperature. The reaction mixture was stirred at room temperature for 4 hrs and quenched with water. It was then extracted with chloroform, washed well with 5% NaS2O3 solution and the organic layer was dried over anhydrous MgSO4. It was filtered and concentrated. The residue was purified by silica-gel column chromatography by eluting it with 30% ethyl acetate:hexane. The product, namely 2-(6-methoxy-1-benzofuran-3-yl)ethyl iodide, was obtained as brown liquid; Yield: 1.2 g (80%); 302 (M+H).

Aufarbeitung

  1. customquenched with water
  2. extractionIt was then extracted with chloroform
  3. washwashed well with 5% NaS2O3 solution
  4. dry with materialthe organic layer was dried over anhydrous MgSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated
  7. customThe residue was purified by silica-gel column chromatography
  8. washby eluting it with 30% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-12a779b3e8ac4efe9bbe4054436b15e0
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235569B2

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