Lithium benzylamide → (Benzylamino)dimethyl(tetramethylcyclopentadienyl)silane

HRID 1421343Notes

Reaction equation

HRID 1421343 reaction equation
Cl[Si:2]([CH3:13])([CH3:12])[C:3]1([CH3:11])[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[C:4]1[CH3:10].[CH2:14]([NH-:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Li+]>CCOCC>[CH2:14]([NH:21][Si:2]([CH3:13])([CH3:12])[C:3]1([CH3:11])[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[C:4]1[CH3:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 10931395Lithium benzylamideHCID 131720376(Tetramethylcyclopentadienyl)dimethylchlorosilane

Product 1

HCID 131720375(Benzylamino)dimethyl(tetramethylcyclopentadienyl)silane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.000 g (4.65; mmol) (chloro)(dimethyl)(tetramethylcyclopentadienyl)silane in 70 mL ether was slowly added 0.526 g (4.651 mmol) lithium benzylamide. The reaction mixture was stirred overnight, then the solvent was removed, the residue was extracted with pentane and filtered. The pentane was removed under reduced pressure to give the product as a pale yellow oil. The yield was 1.234 g (93.3%). Mass spec. m/e 285 (18%). 1H NMR (C6D6) δ 7.0-7.24 (m, 5H), 3.71 (d, 2H), 2.73 (br s, 1H), 1.88 (s, 6H), 1.76 (s, 6H), 0.43 (br t, 1H), -0.07 (s, 6H). 13C NMR (C6D6) δ 144.5, 135.7, 132.0, 128.5, 127.3, 126.7, 56.7, 46.4, 14.6, 11.4, -2.3.

Workup

  1. customthe solvent was removed
  2. extractionthe residue was extracted with pentane
  3. filtrationfiltered
  4. customThe pentane was removed under reduced pressure

Sources & evidence

ORD record
ord-e812aedfbcd74dfa9098b0c40a50b156
Source dataset
uspto-grants-2000_06
Patent number
US06075077

Reaction notes

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