2,5-Dimethylfuran → (1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

HRID 407852

Reaktionsgleichung

Reaktionsgleichung von HRID 407852
[CH3:1][C:2]1[O:3][C:4]([CH3:7])=[CH:5][CH:6]=1.[I-].[Mg+2].[I-].[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:25][CH3:26])=[C:16]([CH:18]2[C:22](=[O:23])[CH:21]=[CH:20][C:19]2=[O:24])[CH:17]=1>ClCCl>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:25][CH3:26])=[C:16]([CH:18]2[C:22](=[O:23])[CH:21]3[CH:20]([C:2]4([CH3:1])[O:3][C:4]3([CH3:7])[CH:5]=[CH:6]4)[C:19]2=[O:24])[CH:17]=1

Komponenten

5

Edukt 3

HCID 122662,5-DimethylfuranHCID 5462737Magnesium diiodideHCID 580614862-(5-Bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione

Produkt 1

HCID 67284135(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,5-Dimethylfuran (2.3 ml, 21.6 mmol) and magnesium iodide (0.40 g, 1.4 mmol) are added to a solution of 2-(5-bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione (2.0 g, 7.2 mmol) in dichloromethane (10 ml) and the mixture is stirred at room temperature for 3 days. The reaction mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1de43f40db744c7caafbcca9766cb8dd
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754242B2

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