2-(4-Fluorophenylmethyl)indene → (2-(4-fluorophenylmethyl)inden-1-yl)-N-(1,1-dimethylethyl)dimethylsilanamine

HRID 11968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11968
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH2:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.C([Li])CCC.[Cl-].[CH3:24][C:25]([NH:28][SiH:29]([CH3:31])[CH3:30])([CH3:27])[CH3:26]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:10]([Si:29]([CH3:31])([CH3:30])[NH:28][C:25]([CH3:27])([CH3:26])[CH3:24])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 219769972-(4-Fluorophenylmethyl)indeneHCID 131725908N-(1,1-dimethylethyl)dimethylsilanamine chlorideHCID 178418339Butyllithium

Produkt 1

HCID 69305488(2-(4-fluorophenylmethyl)inden-1-yl)-N-(1,1-dimethylethyl)dimethylsilanamineAusbeute 97 %

Versuchsvorschrift

To a mixture of 2-(4-fluorophenylmethyl)indene (2.21 g, 9.9 mmol) in 45 mL of hexanes were added 6.5 mL of butyl lithium (1.6 M hexane; 10.4 mmol). The mixture was stirred overnight, the mother liquor decanted and the solid dissolved in THF. To this was added N-(1,1-dimethylethyl)dimethylsilanamine chloride (1.80 g, 10.8 mmol) and the reaction heated at reflux for three hours. The volatiles were removed in vacuo, the residue extracted with hexane, filtered and the volatiles removed in vacuo to give 3.39 g (97 percent) of a yellow oil.

Aufarbeitung

  1. customthe mother liquor decanted
  2. dissolutionthe solid dissolved in THF
  3. temperaturethe reaction heated
  4. temperatureat reflux for three hours
  5. customThe volatiles were removed in vacuo
  6. extractionthe residue extracted with hexane
  7. filtrationfiltered
  8. customthe volatiles removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-db7769977e0f437eb6e215240a68b5d9
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098356B2

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