1-Tetralone → 1-Trimethylsilyloxy-1-cyano-1,2,3,4-tetrahydronaphthalene

HRID 467038

Reaktionsgleichung

Reaktionsgleichung von HRID 467038
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C-:12]#[N:13].[Li+].[CH3:15][Si:16](C#N)([CH3:18])[CH3:17]>C1COCC1>[C:12]([C:1]1([O:11][Si:16]([CH3:18])([CH3:17])[CH3:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)#[N:13]

Komponenten

5

Edukt 3

HCID 107241-TetraloneHCID 75478Lithium cyanideHCID 82115Trimethylsilyl cyanide

Produkt 1

HCID 117469071-Trimethylsilyloxy-1-cyano-1,2,3,4-tetrahydronaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1,2,3,4-tetrahydronaphthalene-1-one (20 g, 140 mmol) in THF (150 mL) was added 6 mL of a 0.5M solution of lithium cyanide (3 mmol, 0.02 equivalent). The reaction mixture was stirred for ~2 minutes and then trimethylsilyl cyanide (25 g, 250 mmol, 1.8 equivalent) was added in one portion. The reaction mixture was stirred for 4.5 hours. Solvents and excess trimethylsilyl cyanide were removed under reduced pressure to give the title compound as a yellow oil. The oil was used in the next step without purification.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 4.5 hours
  2. customSolvents and excess trimethylsilyl cyanide were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-346b244cc9ba41798e732c5fa26a656b
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158948

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