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

HRID 1581734Notes

Reaction equation

HRID 1581734 reaction equation
[Li]CCCC.CCCCCC.[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[C:15]2[C:24]3[C:29]([CH2:30][C:14]1=2)=[CH:28][CH:27]=[CH:26][CH:25]=3.N1C2C(C=CC3C=2C=C2C=3C=CC=C2)=CC=1.[Cl:47][Si:48](Cl)([CH3:50])[CH3:49]>C1COCC1>[Cl:47][Si:48]([CH3:50])([CH3:49])[CH:30]1[C:14]2[N:13]([CH3:12])[C:21]3[C:16]([C:15]=2[C:24]2[C:29]1=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=3

Participants

7

Reactant 5

HCID 6398DichlorodimethylsilaneHCID 8058HexaneHCID 22722361n-Methyl-2-methoxy-5,6-dihydroindeno[2,1-b]indoleHCID 178418339Butyllithium2×HCID 178420856HCID 178420856, compound

Product 1

HCID 22722352Chlorodimethyl(n-methyl-2-methoxy-5,6-dihydroindeno[2,1-b]indol-6-yl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

3.4 mL of a 2.5 M solution of n-BuLi in hexane (8.50 mmol) were added dropwise to a solution of 2.22 g of N-methyl-2-methoxy-5,6-dihydroindeno[2,1-b]indole, obtained as reported above, (Mw=249.32, purity 85.8%, 7.64 mmol; indenoindole: n-BuLi=1:1.1) in 50 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 5 hours. Then it was cooled again to −78° C. and added dropwise to a solution of dichlorodimethylsilane (Mw=129.06, d=1.064, 0.92 mL, 7.64 mmol; indenoindole: Me2SiCl2=1:1) in 20 mL of THF, previously cooled to −78° C. At the end of the addition, the dark brown solution was allowed to warm up to room temperature and stirred overnight. The solvents were evaporated under reduced pressure to give the desired product, containing few by-products, in the form of a brown sticky solid; this product was used in the following 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

Sources & evidence

ORD record
ord-9d14bcbd2f9441b0b3c7912e56b43b56
Source dataset
uspto-grants-2004_05
Patent number
US06730754B2

Reaction notes

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