1-Tetralone → 1-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 414177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414177
C[Si]([C:5]#[N:6])(C)C.[C:7]1(=[O:17])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1.[Li]>C1COCC1.[I-].[Zn+2].[I-]>[OH:17][C:7]1([CH2:5][NH2:6])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1

Komponenten

6

Edukt 3

HCID 107241-TetraloneHCID 82115Trimethylsilyl cyanideHCID 3028194Lithium

Produkt 1

HCID 129148591-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-olAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9883512zinc(II)iodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Five and one-half g of trimethylsilylcyanide is added to a mixture of 7.3 g of 1-tetralone and 10 mg of zinc iodide. The mixture is stirred at room temperature overnight. It is dissolved in 25 ml dry THF and slowly added to a suspension of 2.3 g of lithium aluminumhydride in 40 ml of THF. Reaction is refluxed for three hours and upon cooling, carefully quenched with water. Precipitate is filtered and aqueous solution is diluted with 100 ml 1N NaOH. It was extracted with ether (3×100 ml), dried over anhydrous MgSO4, filtered, and ether evaporated yielding an oil which solidifies upon standing giving 6.4 g (73%) of (1-hydroxy-1,2,3,4-tetrahydronaphthyl)methylamine.

Aufarbeitung

  1. customReaction
  2. temperatureis refluxed for three hours
  3. temperatureupon cooling
  4. customcarefully quenched with water
  5. filtrationPrecipitate is filtered
  6. additionaqueous solution is diluted with 100 ml 1N NaOH
  7. extractionIt was extracted with ether (3×100 ml)
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. customether evaporated
  11. customyielding an oil which

Quellen und Nachweise

ORD-Eintrag
ord-329f329a0cdd4493b7078fea42a259cc
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04791103

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