Dichlorodimethylsilane → HCID 59735669, compound

HRID 2105748Notes

Reaction equation

HRID 2105748 reaction equation
[Li]CCCC.CCCCCC.[CH3:12][C:13]1[CH2:14][C:15]2[C:20]([CH:21]=1)=[C:19]([CH3:22])[CH:18]=[C:17]([CH3:23])[CH:16]=2.[Si:24]([CH3:28])([CH3:27])(Cl)[Cl:25].[Li]>CCOCC.C1COCC1>[Cl:25][Si:24]([CH:14]1[C:15]2[C:20](=[C:19]([CH3:22])[CH:18]=[C:17]([CH3:23])[CH:16]=2)[CH:21]=[C:13]1[CH3:12])([CH3:28])[CH3:27]

Participants

8

Reactant 5

HCID 6398DichlorodimethylsilaneHCID 8058HexaneHCID 3028194LithiumHCID 109207862,4,6-trimethyl-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 59735669HCID 59735669, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 2.5 M n-BuLi solution in hexane (37.2 mL, 0.093 mol) was added dropwise at 0° C. under nitrogen atmosphere to a solution of 14.00 g of 2,4,6-trimethyl-indene (prepared according to Eur. Pat. Appl. 693,506) in 100 mL of Et2O in a 500 mL 3-necked round flask. During the addition a white suspension was formed. The mixture was then allowed to warm up to r.t. and stirred for 30 min, with final formation of a white suspension. Then a solution of Me2SiCl2 (98%, d=1,064, 11.28 mL, 0.093 mol.) in 30 mL of THF was cooled to 0° C. and slowly added to the lithium salt suspension, also cooled to 0° C. The reaction mixture was allowed to warm up to r.t. and stirred for 2 h with final formation of a light yellow suspension. The solvents were then removed in vacuo and the residue was extracted with 150 mL of toluene to remove the LiCl. The light yellow filtrate was brought to dryness in vacuo to give 21.53 g of a yellow oil, characterized by 1NMR analysis as the target product, yield 97.5%. This product was used as such in the next step without further purification.

Workup

  1. additionDuring the addition a white suspension
  2. customwas formed
  3. temperaturealso cooled to 0° C
  4. temperatureto warm up to r.t.
  5. stirringstirred for 2 h with final formation of a light yellow suspension
  6. customThe solvents were then removed in vacuo
  7. extractionthe residue was extracted with 150 mL of toluene
  8. customto remove the LiCl

Sources & evidence

ORD record
ord-f92f639f6d50436d89067481a1f4068c
Source dataset
uspto-grants-2009_08
Patent number
US07579423B2

Reaction notes

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