Water → 2-Ethynylbenzaldehyde

HRID 1644714

Reaktionsgleichung

Reaktionsgleichung von HRID 1644714
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8].[F-].[K+].O>CN(C)C=O>[C:4]([C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])#[CH:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 522689Potassium FluorideHCID 27716412-[(Trimethylsilyl)ethynyl]benzaldehyde

Produkt 1

HCID 6403682-EthynylbenzaldehydeAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-trimethylsilanylethynyl-benzaldehyde (6 g, 29.70 mmol) in N,N-dimethylformamide (10 mL) was added potassium fluoride (1 g, 17.2 mmol). The reaction mixture was stirred at room temperature for 30 minutes. The resulting solution was poured into water, and then extracted with dichloromethane. The collected organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 0-25% ethyl acetate in hexane) gave 2-ethynyl-benzaldehyde (2.8 g, 73%) as a white solid. MS (ESI+) cald for C9H6O [(M+H)+] 130, obsd. 131.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialThe collected organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4a229ec1613549fa8e1930ca217e09d5
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124629B2

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