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

HRID 407856Notes

Reaction equation

HRID 407856 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.[I-].[Mg+2].[I-].[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[CH:19]1[C:23](=[O:24])[CH:22]=[CH:21][C:20]1=[O:25]>ClCCl>[Br:1][C:2]1[CH:3]2[O:4][CH:5]([CH:6]=1)[CH:21]1[CH:22]2[C:23](=[O:24])[CH:19]([C:12]2[C:11]([CH3:10])=[CH:16][C:15]([CH3:17])=[CH:14][C:13]=2[CH3:18])[C:20]1=[O:25]

Participants

5

Reactant 3

HCID 891643-BromofuranHCID 5462737Magnesium diiodideHCID 666844242-(2,4,6-Trimethylphenyl)cyclopent-4-ene-1,3-dione

Product 1

HCID 67284125(1RS, 2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Bromofuran (5.2 g, 56 mmol) and magnesium iodide (1.5 g, 5.6 mmol) are added to 2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (4.0 g, 18.7 mmol) and the mixture is stirred at room temperature for 2 days; small quantities of dichloromethane are added when required to aid stirring. The reaction mixture is allowed to stand at room temperature for 17 hours, then concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS, 2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione.

Workup

  1. stirringto aid stirring
  2. waitto stand at room temperature for 17 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3f6249c8f1ef4ca0ad83b3146435265c
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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