Dichlorodimethylsilane → Dimethyl(2-methyl-4-phenylindenyl)silyl chloride

HRID 2216716Notes

Reaction equation

HRID 2216716 reaction equation
[Li]CCCC.CCCCCC.[CH3:12][C:13]1[CH2:14][C:15]2[C:20]([CH:21]=1)=[C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:18]=[CH:17][CH:16]=2.[Cl:28][Si:29](Cl)([CH3:31])[CH3:30]>CCOCC>[Cl:28][Si:29]([CH:14]1[C:15]2[C:20](=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[CH:21]=[C:13]1[CH3:12])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 6398DichlorodimethylsilaneHCID 8058HexaneHCID 110745592-Methyl-4-phenylindeneHCID 178418339Butyllithium

Product 1

HCID 21943894Dimethyl(2-methyl-4-phenylindenyl)silyl chlorideYield 92.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 2.5 M solution of n-BuLi in hexane (4.85 mL, 12.12 mmol) was added at 0° C. to a solution of 2.50 g of 2-methyl-4-phenyl-indene (Boulder Scientific Company, Mw=206.29, 12.12 mmol, n-BuLi:2-Me-4-Ph-Ind=1:1) in 30 mL of ether. The resulting mixture was stirred for additional 2 h at room temperature with final formation of an orange solution. This solution was cooled again to 0° C. and added slowly of a solution of 1.58 mL of dichlorodimethylsilane (Aldrich, Mw=129.06, d=1.064, 13.03 mmol, Me2SiCl2:2-Me-4-Ph-Ind=1.08:1) in 20 mL of ether. The reaction mixture was then allowed to warm to room temperature and stirred for 1 h. The final straw yellow suspension was concentrated under vacuum and the residue was extracted with 50 mL of toluene. The extract was dried under vacuum to give 3.36 g of a straw yellow solid, which was characterized by GC-MS analysis and 1H-NMR spectroscopy. Yield=92.8%.

Workup

  1. temperatureThis solution was cooled again to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 h
  4. concentrationThe final straw yellow suspension was concentrated under vacuum
  5. extractionthe residue was extracted with 50 mL of toluene
  6. customThe extract was dried under vacuum

Sources & evidence

ORD record
ord-b18473d95c754a5895d2f865aaea420d
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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