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

HRID 2185083Notes

Reaction equation

HRID 2185083 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-9792609c66f94909bd6c36c854ce1d6d
Source dataset
uspto-grants-2002_06
Patent number
US06399723B1

Reaction notes

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