Furan → HCID 66709766, compound

HRID 1193031Notes

Reaction equation

HRID 1193031 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]2=[O:22])=[C:11]([CH3:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:24]1[CH:28]=[CH:27][CH:26]=[CH:25]1.[I-].[Mg+2].[I-]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]2[C:17](=[O:22])[CH:18]3[CH:19]([CH:25]4[O:24][CH:28]3[CH:27]=[CH:26]4)[C:20]2=[O:21])=[C:11]([CH3:23])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8029FuranHCID 5462737Magnesium diiodideHCID 58070832HCID 58070832, compound

Product 1

HCID 66709766HCID 66709766, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-(4-benzyloxy-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione (1 g, 3.3 mmol), furan (20 ml) and magnesium iodide (50 mg) is stirred at room temperature for 5 days. The reaction mixture is diluted with methanol and silica gel is added. After evaporation of the solvent, the residue is purified by column chromatography on silica gel to give 4-(4-benzyloxy-2,6-dimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (0.531 g).

Workup

  1. additionis added
  2. customAfter evaporation of the solvent
  3. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-03e1425b4b28466f823d8d608a77724e
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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