Sodium Carbonate → 5-Ethynyl-4-(4-fluoro-phenyl)-1-methyl-1H-[1,2,3]triazole

HRID 402421Notes

Reaction equation

HRID 402421 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH:14]=O)=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].COP(C(=[N+]=[N-])C(=O)C)(=O)OC.C(=O)([O-])[O-].[Na+].[Na+]>CO>[C:14]([C:9]1[N:10]([CH3:13])[N:11]=[N:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)#[CH:16]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 866647645-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazole-4-carbaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 866647655-Ethynyl-4-(4-fluoro-phenyl)-1-methyl-1H-[1,2,3]triazoleYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carbaldehyde (616 mg, 3.0 mmol) in MeOH (13 mL) was added potassium carbonate (829 mg, 6.0 mmol) followed by a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (634 mg, 3.3 mmol) in MeOH (4 mL) at room temperature and the resulting mixture stirred for 1 h. The mixture was then poured into sodium carbonate solution (1 M) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (556 mg, 92%) as a light red solid. MS: m/e=202.2 [M]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe combined organic extracts washed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-8bf8c5759e0e43888ef37fa509d447f7
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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