Dichlorodimethylsilane → 4-(3,5-Dimethylphenyl)-2-isopropylindene

HRID 842535Notes

Reaction equation

HRID 842535 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]([CH:23]([CH3:25])[CH3:24])[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]([CH:23]([CH3:25])[CH3:24])[CH2:18]3)[CH:8]=[C:7]([CH3:6])[CH:12]=1

Participants

4

Reactant 2

HCID 6398DichlorodimethylsilaneHCID 22023013Lithium 4-(3,5-dimethylphenyl)-2-isopropylindenide

Product 1

HCID 220230144-(3,5-Dimethylphenyl)-2-isopropylindeneYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

SiMe2Cl2 (0.69 g, 5.4 mmol) was dissolved in 80 mL of THF. While stirring, lithium 4-(3′,5′-dimethylphenyl)-2-isopropylindenide (2.9 g, 11 mmol) was added as a dry powder and the contents allowed to stir overnight at room temperature. The solvent was removed in vacuo and the residue was taken up in pentane and filtered to removed LiCl salts. The pentane was removed in vacuo to yield a flaky white solid (2.1 g, 67%).

Workup

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

Sources & evidence

ORD record
ord-4f62123f8bf64b76829e415a355d7305
Source dataset
uspto-grants-2002_04
Patent number
US06376407B1

Reaction notes

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