2-Methyl-4-phenylindene → (2-Methyl-4-phenylindenyl)(t-butylamino)dimethylsilane

HRID 850128Notes

Reaction equation

HRID 850128 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:7]=[CH:6][CH:5]=2.[CH3:17][SiH:18]([N:20](Cl)[C:21]([CH3:24])([CH3:23])[CH3:22])[CH3:19]>C1COCC1>[CH3:1][C:2]1[CH:3]([Si:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:17])[C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 110745592-Methyl-4-phenylindeneHCID 123286153Dimethylsilyl(t-butylamino)chloride

Product 1

HCID 19366102(2-Methyl-4-phenylindenyl)(t-butylamino)dimethylsilaneYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2-methyl-4-phenylindene (synthesized substantially according to the technique reported in U.S. Pat. No. 5,329.033) (3.00 g, 0.014 moles) in THF (10 mL) was added dropwise to a stirring solution of KH (0.601 g, 0.0150 moles) in THF (50 mL). This mixture was allowed to stir for 16 hours. The solution was then filtered and added dropwise to a solution of dimethylsilyl(t-butylamino)chloride (2.41 g, 0.0145 moles) in THF (75 mL). This mixture was allowed to stir for 16 hours. After the reaction period the volatiles were removed and the residue extracted and filtered using hexane. Removal of the volatiles resulted in the isolation of the desired product as a light yellow oil (4.00 g, 82.0 percent).

Workup

  1. filtrationThe solution was then filtered
  2. stirringto stir for 16 hours
  3. customAfter the reaction period the volatiles
  4. customwere removed
  5. extractionthe residue extracted
  6. filtrationfiltered
  7. customRemoval of the volatiles

Sources & evidence

ORD record
ord-3ab94c12469443d7acbbcb2807abbccd
Source dataset
uspto-grants-2000_01
Patent number
US06015868

Reaction notes

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