Methanol → 4-Methyl-7-propyl-1H-indene

HRID 1613915Notes

Reaction equation

HRID 1613915 reaction equation
C[O-].[Na+].CO.[CH3:6][C:7](=O)[CH2:8][CH2:9][C:10](=O)[CH2:11][CH2:12][CH3:13].[CH:16]1[CH2:20][CH:19]=[CH:18][CH:17]=1>>[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][CH2:12][CH3:13])=[C:16]2[C:17]=1[CH:18]=[CH:19][CH2:20]2

Participants

5

Reactant 4

HCID 887MethanolHCID 7612CyclopentadieneHCID 64203992,5-OctanedioneHCID 10942334Sodium Methoxide

Product 1

HCID 187834694-Methyl-7-propyl-1H-indeneYield 39.5%

Procedure

45 ml of a 30 percent strength solution of sodium methanolate in methanol (250 mmol) were initially introduced into the reaction vessel at 0° C., and a mixture of 14.2 g (100 mmol) of 2,5-octanedione and 9 ml (110 mmol) of cyclopentadiene was added in the course of 30 minutes. After the mixture had been stirred at room temperature for 3 hours, it was poured into 300 ml of ice-water and extracted with diethyl ether and the organic phase was dried over magnesium sulfate. The residue which remained after evaporation was chromatographed on silica gel. 6.8 g (39%) of the indene 2 could be isolated with hexane as the mobile phase.

Workup

  1. additionwas added in the course of 30 minutes
  2. extractionextracted with diethyl ether
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. customafter evaporation
  5. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-cf407bff8f754ea5a2df81568822819b
Source dataset
uspto-grants-1993_03
Patent number
US05194619

Reaction notes

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