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

HRID 1588717

Reaktionsgleichung

Reaktionsgleichung von HRID 1588717
C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].[CH:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OCC)C>O1CCCC1.O>[CH3:11][Si:12]([C:15]#[C:16][CH:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:24])([CH3:14])[CH3:13]

Komponenten

7

Edukt 4

HCID 240BenzaldehydeHCID 3283Diethyl EtherHCID 66111TrimethylsilylacetyleneHCID 57426343Lithium bis(trimethylsilyl)amide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Place lithium hexamethyldisilazane (12 mL of a IM solution in tetrahydrofuran, 12 mmol) under an argon atmosphere and cool to 0° C. Add trimethylsilylacetylene (1.7 mL, 12 mmol) and stir for 1 hour at 0° C. Add benzaldehyde (1.06 g, 10 mmol) in tetrahydrofuran (25 mL). Allow to warm to room temperature and stir for 3 hours. Pour the mixture into ethyl ether and water, separate the organic phase and evaporate the solvent in vacuo. Filter the oil through silica gel (20% ethyl acetate/hexane) and evaporate the solvent in vacuo to yield the title compound.

Aufarbeitung

  1. customseparate the organic phase
  2. customevaporate the solvent in vacuo
  3. filtrationFilter the oil through silica gel (20% ethyl acetate/hexane)
  4. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fa6f0d3aed2a43f7a7782b5724257895
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223518

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