Chlorotrimethylsilane → HCID 59270598, compound

HRID 446215Notes

Reaction equation

HRID 446215 reaction equation
[CH2:1]([C:8]1[CH:26]=[CH:25][C:11]([N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.Cl[Si:33]([CH3:36])([CH3:35])[CH3:34].CCCCCC>O1CCCC1>[C:13]1([N:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:11]2[CH:10]=[CH:9][C:8]([CH:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[Si:33]([CH3:36])([CH3:35])[CH3:34])=[CH:26][CH:25]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 233994894-benzyl-N,N-diphenylanilineHCID 178418339Butyllithium

Product 1

HCID 59270598HCID 59270598, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-benzyl-N,N-diphenylaniline (5.0 g, 14.9 mmol) was dissolved in tetrahydrofuran (80 mL) under a nitrogen atmosphere. n-Butyllithium (10.3 mL, 16.4 mmol) was slowly added to the reaction solution at −78° C., and then the reaction mixture solution was stirred at room temperature for 1 hour. Also, the reaction mixture solution with chlorotrimethylsilane (1.8 g, 16.4 mmol) added thereto was stirred at room temperature for 1 hour. The reaction mixture solution was passed through a silica gel column by using hexane as an eluant. After the solvent is removed, the residue material was dried in vacuum to thereby a white solid (5.1 g, yield: 84%).

Workup

  1. stirringthereto was stirred at room temperature for 1 hour
  2. customAfter the solvent is removed

Sources & evidence

ORD record
ord-1d69b4af7e174f138d876dfe8dc606d9
Source dataset
uspto-grants-2013_07
Patent number
US08476474B2

Reaction notes

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