Cyclopentadiene → HCID 19774604, compound

HRID 1613916Notes

Reaction equation

HRID 1613916 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[CH3:6][C:7](=O)[CH2:8][CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CO>[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:1]2[C:2]=1[CH:3]=[CH:4][CH2:5]2

Participants

4

Reactant 2

HCID 7612CyclopentadieneHCID 13619354HCID 13619354, compound

Product 1

HCID 19774604HCID 19774604, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

9 ml (110 mmol) of cyclopentadiene were added to a solution of 28.0 g (250 mmol) of potassium t-butylate in 50 ml of methanol at 0° C. 21.2 g (100 mmol) of 2,5-tridecanedione were then added dropwise at 0° C. After the mixture had been stirred at 0° C. for 1 hour, it was stirred at room temperature for a further 3 hours. Working up was carried out analogously to Example 6. Column chromatography gave 16.9 g (70 %) of the indene 5.

Workup

  1. stirringit was stirred at room temperature for a further 3 hours

Sources & evidence

ORD record
ord-813947e5926840c592da0f7cba63970a
Source dataset
uspto-grants-1993_03
Patent number
US05194619

Reaction notes

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