Cyclopentadiene → HCID 19774595, compound

HRID 1613921Notes

Reaction equation

HRID 1613921 reaction equation
C[O-].[Na+].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9](=O)[CH2:10][CH2:11][C:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)=O.[CH:20]1[CH2:24][CH:23]=[CH:22][CH:21]=1>CO.CS(C)=O>[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[CH:10]=[CH:11][C:12]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)=[C:20]2[C:21]=1[CH:22]=[CH:23][CH2:24]2

Participants

6

Reactant 3

HCID 7612CyclopentadieneHCID 4347661HCID 4347661, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 19774595HCID 19774595, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

18.9 ml of a 30 percent strength solution of sodium methanolate (105 mmol) in methanol was initially introduced into the reaction vessel at 0° C, and a solution of 9.2 g (42.2 mmol) of 1,4-bis(2-furyl)-1,4-butanedione and 3.8 ml (46.2 mmol) of cyclopentadiene in DMSO were added dropwise in the course of 1 hour. After the mixture had been stirred at room temperature for 45 minutes it was poured onto ice-water and extracted with diethyl ether. After drying and evaporation, the residue was chromatographed on silica gel. 3.0 g (29 %) of the indene 14 could be obtained with hexane/methylene chloride (2:1) as the mobile phase.

Workup

  1. additionwas poured onto ice-water
  2. extractionextracted with diethyl ether
  3. customAfter drying
  4. customevaporation
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-fe2baba37dda40c9aa19f74607b1b946
Source dataset
uspto-grants-1993_03
Patent number
US05194619

Reaction notes

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