Lithium benzylamide → (Benzylamino)dimethyl(tetramethylcyclopentadienyl)silane

HRID 1816471Notes

Reaction equation

HRID 1816471 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 (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-c7370ced75734370bda0ffaf8e03aeef
Source dataset
uspto-grants-2005_04
Patent number
US06884857B1

Reaction notes

Loading…