Indene → 1H-Indene, (1-methylethylidene)bis-

HRID 1738593Notes

Reaction equation

HRID 1738593 reaction equation
C([Li])CCC.[CH2:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.[C:15](=[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19]1)([CH3:17])[CH3:16]>O>[CH:6]1([C:15]([CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19]2)([CH3:17])[CH3:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 7219IndeneHCID 1186931-(1-Methylethylidene)-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 117806711H-Indene, (1-methylethylidene)bis-Yield 13%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18.8 cm3 (47.0 mmol) of n-butyllithium were added at 0° C. to a solution of 5.93 g (47.0 mmol) of indene (industrial, 91% pure) filtered over Al2O3. After the mixture had been stirred at room temperature for 15 minutes, the solution was slowly added dropwise to a solution of 7.40 g (47.0 mmol) of 1-isopropylideneindene. After the mixture had been stirred at room temperature for 2 hours, 50 cm3 of water were added and the mixture was extracted with diethyl ether. The yellow organic phase was dried over MgSO4. The residue which remained after the solvent had been stripped off was chromatographed on silica gel 60. 1.5 g (13%) of the product (2 isomers) could be isolated with hexane/methylene chloride (10:1).

Workup

  1. filtrationfiltered over Al2O3
  2. stirringAfter the mixture had been stirred at room temperature for 2 hours
  3. extractionthe mixture was extracted with diethyl ether
  4. dry with materialThe yellow organic phase was dried over MgSO4
  5. customwas chromatographed on silica gel 60

Sources & evidence

ORD record
ord-2398ef3c656140caa3625bc79a5eb842
Source dataset
uspto-grants-1999_10
Patent number
US05962719

Reaction notes

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