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

HRID 842513Notes

Reaction equation

HRID 842513 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-7fcdd167511e449180991d2f72a633b1
Source dataset
uspto-grants-2002_04
Patent number
US06376410B1

Reaction notes

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