Dichlorodimethylsilane → 4-(3',5'-Dimethylphenyl)2-methylindene

HRID 2185076Notes

Reaction equation

HRID 2185076 reaction equation
[Si](Cl)(Cl)(C)C.[CH3:6][C:7]1[CH:8]=[C:9]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[C:17]([CH3:23])[CH-:18]3)[CH:10]=[C:11]([CH3:13])[CH:12]=1.[Li+]>C1COCC1>[CH3:13][C:11]1[CH:10]=[C:9]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[C:17]([CH3:23])[CH2:18]3)[CH:8]=[C:7]([CH3:6])[CH:12]=1

Participants

4

Reactant 2

HCID 6398DichlorodimethylsilaneHCID 22023088Lithium 4-(3,5-dimethylphenyl)-2-methylindenide

Product 1

HCID 179395644-(3',5'-Dimethylphenyl)2-methylindeneYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

SiMe2Cl2 (1.2 g, 9.4 mmol) was dissolved in 80 mL of THF. While stirring, lithium 4-(3,5-dimethylphenyl)-2-methylindenide (4.5 g, 18.7 mmol) was added as a dry powder and the contents were allowed to stir overnight at room temperature. The solvent was removed in vacuo and the residue was taken up in pentane and filtered to remove LiCl salts. The pentane was removed in vacuo to yield a flaky white solid (4.23 g, 87%).

Workup

  1. stirringto stir overnight at room temperature
  2. customThe solvent was removed in vacuo
  3. filtrationfiltered
  4. customto remove LiCl salts
  5. customThe pentane was removed in vacuo

Sources & evidence

ORD record
ord-fb85dbd2129b4c59af4815075c09fb48
Source dataset
uspto-grants-2002_06
Patent number
US06399723B1

Reaction notes

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