Potassium Carbonate → 2-Ethynyl-5-fluoropyridine

HRID 402385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402385
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=O)=[N:6][CH:7]=1.[C:10](=O)([O-])[O-].[K+].[K+].COP(C(=[N+]=[N-])C(=O)C)(=O)OC>CO>[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1)#[CH:10]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 103516975-Fluoropyridine-2-carboxaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Produkt 1

HCID 447549262-Ethynyl-5-fluoropyridineAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a mixture of 5-fluoro-2-formylpyridine (1.10 g, 9.0 mmol) in MeOH (38 mL) was added potassium carbonate (2.44 g, 0.018 mol) followed by a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (2.03 g, 11 mmol) in MeOH (12 mL). The mixture was stirred at room temperature for 90 min, then extracted with diethylether. The organic layers were then washed with sodium hydrogen carbonate solution (1 M) and brine, dried over sodium sulfate, filtered and evaporated at to give the title compound (1.01 g, 78%) as a light brown liquid. MS: m/e=121.0 [M]+.

Aufarbeitung

  1. extractionextracted with diethylether
  2. washThe organic layers were then washed with sodium hydrogen carbonate solution (1 M) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated at

Quellen und Nachweise

ORD-Eintrag
ord-69f06fc6badf468098d511f27e2b9daf
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742097B2

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