Dichlorodimethylsilane → Chlorodimethyl(n-methyl-2-methyl-5,6-dihydroindeno[2,1-b]indol-6-yl)silane

HRID 1581731Notes

Reaction equation

HRID 1581731 reaction equation
[Li]CCCC.CCCCCC.[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH3:22])=[CH:19][CH:20]=2)[C:15]2[C:23]3[C:28]([CH2:29][C:14]1=2)=[CH:27][CH:26]=[CH:25][CH:24]=3.N1C2C(C=CC3C=2C=C2C=3C=CC=C2)=CC=1.[Cl:46][Si:47](Cl)([CH3:49])[CH3:48]>C1COCC1>[Cl:46][Si:47]([CH3:49])([CH3:48])[CH:29]1[C:14]2[N:13]([CH3:12])[C:21]3[C:16]([C:15]=2[C:23]2[C:28]1=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][C:18]([CH3:22])=[CH:19][CH:20]=3

Participants

7

Reactant 5

HCID 6398DichlorodimethylsilaneHCID 8058HexaneHCID 155337292,5-Dimethyl-5,6-dihydroindeno[2,1-b]indoleHCID 178418339Butyllithium2×HCID 178420856HCID 178420856, compound

Product 1

HCID 22722355Chlorodimethyl(n-methyl-2-methyl-5,6-dihydroindeno[2,1-b]indol-6-yl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

9.5 mL of a 2.5 M solution of n-BuLi in hexane (23.75 mmol) were added dropwise to a solution of 5.1 g of N-methyl-2-methyl-5,6-dihydroindeno[2,1-b]indole, obtained as reported above, (purity 98.2%, Mw=233.32, 21.46 mmol; indenoindole: n-BuLi=1:1.1) in 70 mL of THF, previously cooled to −78° C. At the end of the addition, the brown solution was allowed to warm up to room temperature and stirred for 6 hours. Then it was cooled again to −78° C. and added dropwise to a solution of dichlorodimethylsilane (Mw=129.06, d=1.064, 2.6 mL, 21.43 mmol; indenoindole: Me2SiCl2=1:1) in 20 mL of THF, previously cooled to −78° C. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred overnight. The solvents were evaporated under reduced pressure to give a brown sticky solid, which at the 1H-NMR analysis resulted to be the target product, with few by-products. The product was used in the subsequent step without further purification.

Workup

  1. customobtained
  2. additionAt the end of the addition
  3. temperatureto warm up to room temperature
  4. temperatureThen it was cooled again to −78° C.
  5. temperaturepreviously cooled to −78° C
  6. additionAt the end of the addition
  7. temperatureto warm up to room temperature
  8. stirringstirred overnight
  9. customThe solvents were evaporated under reduced pressure
  10. customto give a brown sticky solid, which at the 1H-NMR analysis
  11. customresulted
  12. customThe product was used in the subsequent step without further purification

Sources & evidence

ORD record
ord-b028dc6e860d4855b92625b7b613b900
Source dataset
uspto-grants-2004_05
Patent number
US06730754B2

Reaction notes

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