Lithium benzylamide → (Benzylamino)dimethyl(tetramethylcyclopentadienyl)silane

HRID 1941439Notes

Reaction equation

HRID 1941439 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 (4.651 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 (C6 D6) 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-dce7a4de99cd4fe5b68dbdd2323987e7
Source dataset
uspto-grants-1997_12
Patent number
US05703187

Reaction notes

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