Benzaldehyde → 1-Phenyl-3-(trimethylsilyl)-2-propyn-1-ol

HRID 1654756

Reaktionsgleichung

Reaktionsgleichung von HRID 1654756
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C[Si](C)(C)N[Si](C)(C)C.[Li].[C-]#[C-].[Li+].[Li+].[CH:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH3:1][Si:2]([C:5]#[C:6][CH:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[OH:28])([CH3:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 66111TrimethylsilylacetyleneHCID 57426343Lithium bis(trimethylsilyl)amideHCID 178462446HCID 178462446, Verbindung

Produkt 1

HCID 27604161-Phenyl-3-(trimethylsilyl)-2-propyn-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In step a, trimethylsilylacetylene (1) can first be reacted with a non-nucleophilic base, such as lithium hexamethyldisilazane, in a suitable aprotic solvent, such as tetrahydrofuran. The resulting lithium acetylide can then be reacted with the appropriate benzaldehyde compound of structure 2 to give the corresponding α-[(trimethylsilyl)ethynyl]-benzenemethanol compound of structure 3.

Quellen und Nachweise

ORD-Eintrag
ord-a4bd6d5991e44ca787171a8d519a9802
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05409942

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