Dichlorodimethylsilane → HCID 59735669, compound

HRID 2425313Notes

Reaction equation

HRID 2425313 reaction equation
[Li]CCCC.[CH3:6][C:7]1[CH2:8][C:9]2[C:14]([CH:15]=1)=[C:13]([CH3:16])[CH:12]=[C:11]([CH3:17])[CH:10]=2.[Si:18]([CH3:22])([CH3:21])(Cl)[Cl:19].[Li]>CCCCCC.CCOCC.C1COCC1>[Cl:19][Si:18]([CH:8]1[C:9]2[C:14](=[C:13]([CH3:16])[CH:12]=[C:11]([CH3:17])[CH:10]=2)[CH:15]=[C:7]1[CH3:6])([CH3:22])[CH3:21]

Participants

8

Reactant 4

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

Product 1

HCID 59735669HCID 59735669, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A 2.5 M n-BuLi solution in hexane (9.6 mL) was added dropwise at 0° C. under nitrogen to a solution of 3.6 g of 2,4,6-trimethylindene in 35 mL of Et2O. During the addition a white-off suspension was formed. After 10 min the mixture was allowed to warm up to r.t. and stirred for 30 min, with final formation of a white suspension. Then a solution of Me2SiCl2 (4 mL) in 35 mL of THF was cooled to 0° C. and slowly added to the lithium salt suspension, also cooled to 0° C. After 30 min the yellow reaction mixture was allowed to warm up to r.t. and stirred for 24 h. Then the solvents were removed in vacuo and the light orange oil with a powder was characterized by 1H-NMR spectroscopy. The product was used as such in the next step without further purification.

Workup

  1. additionDuring the addition a white-off suspension
  2. customwas formed
  3. temperaturealso cooled to 0° C
  4. waitAfter 30 min the yellow reaction mixture was allowed
  5. temperatureto warm up to r.t.
  6. stirringstirred for 24 h
  7. customThen the solvents were removed in vacuo
  8. customwithout further purification

Sources & evidence

ORD record
ord-2f07651d63e64255823baeb08801fae1
Source dataset
uspto-grants-2011_06
Patent number
US07964679B2

Reaction notes

Loading…