Water → 2-Ethynylbenzaldehyde

HRID 1644714

Reaction equation

HRID 1644714 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 6403682-EthynylbenzaldehydeYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-4a229ec1613549fa8e1930ca217e09d5
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Linked notes

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