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

HRID 407845Notes

Reaction equation

HRID 407845 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[I-].[Mg+2].[I-].[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[CH:18]1[C:22](=[O:23])[CH:21]=[CH:20][C:19]1=[O:24]>>[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[CH:18]1[C:19](=[O:24])[CH:20]2[CH:21]([CH:5]3[O:1][CH:2]2[CH:3]=[CH:4]3)[C:22]1=[O:23]

Participants

4

Reactant 3

HCID 8029FuranHCID 5462737Magnesium diiodideHCID 666844242-(2,4,6-Trimethylphenyl)cyclopent-4-ene-1,3-dione

Product 1

HCID 67283862(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

Procedure

Furan (214 ml, 3.15 mol) and magnesium iodide (7.0 g, 0.025 mol) are added to 2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (27.0 g, 0.126 mol) and the mixture is stirred at room temperature for 4 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-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione.

Workup

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

Sources & evidence

ORD record
ord-841935e5c7b9426fa33c9701f42364c3
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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