Cyclopentadiene → HCID 19774599, compound

HRID 1613918Notes

Reaction equation

HRID 1613918 reaction equation
[CH3:1][C:2]([CH3:14])([C:4](=O)[CH2:5][CH2:6][C:7](=O)[C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:3].[CH:15]1[CH2:19][CH:18]=[CH:17][CH:16]=1.C[O-].[Na+]>CO>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[C:15]2[C:16]=1[CH:17]=[CH:18][CH2:19]2)([CH3:14])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 7612CyclopentadieneHCID 108218252,2,7,7-tetraMethyl-3,6-octanedioneHCID 10942334Sodium Methoxide

Product 1

HCID 19774599HCID 19774599, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 14.8 g (74.6 mmol) of 2,2,7,7-tetramethyl-3,6-octanedione and 6.7 ml (82.1 mmol) of cyclopentadiene was added to 34.3 ml of a 30 percent strength solution of sodium methanolate (186 mmol) in methanol at 0° C. in the course of 10 minutes. After the mixture had been stirred at room temperature for 30 hours, it was hydrolyzed and extracted with methylene chloride. After drying over MgSO4, the product was evaporated to dryness. Column chromatography on silica gel with hexane as the mobile phase gave 1.75 g (10 %) of the indene 10. For the NMR data, see Table 1.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialAfter drying over MgSO4
  3. customthe product was evaporated to dryness

Sources & evidence

ORD record
ord-dce9a607792748aa9dd71edf82abeefd
Source dataset
uspto-grants-1993_03
Patent number
US05194619

Reaction notes

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