Potassium Carbonate → 2-Ethynyl-5-fluoropyridine

HRID 402385Notes

Reaction equation

HRID 402385 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 447549262-Ethynyl-5-fluoropyridineYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-69f06fc6badf468098d511f27e2b9daf
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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