Diethyl Ether → (Benzylamino)dimethyl(tetramethylcyclopenta-dienyl)silane

HRID 2119991Notes

Reaction equation

HRID 2119991 reaction equation
Cl[Si:2]([CH3:13])([CH3:12])[C:3]1(C)[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+].[CH3:23]COCC>>[CH2:14]([NH:21][Si:2]([CH3:12])([CH3:13])[C:3]1[CH:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH3:8])[C:7]=1[CH3:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 10931395Lithium benzylamideHCID 131720376(Tetramethylcyclopentadienyl)dimethylchlorosilane

Product 1

HCID 22494460(Benzylamino)dimethyl(tetramethylcyclopenta-dienyl)silane

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-9392adb877a74604a5890c0b12555dd6
Source dataset
uspto-grants-2004_02
Patent number
US06686488B2

Reaction notes

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