Trimethylsilyldiazomethane → Methyl 5,6-dimethylpicolinate

HRID 68555Notes

Reaction equation

HRID 68555 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH3:8][C:9]1[CH:10]=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[N:13][C:14]=1[CH3:15]>CCCCCC.CO.ClCCl>[CH3:1][O:17][C:16]([C:12]1[CH:11]=[CH:10][C:9]([CH3:8])=[C:14]([CH3:15])[N:13]=1)=[O:18]

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 132095705,6-Dimethylpyridine-2-carboxylic acid

Product 1

HCID 22417656Methyl 5,6-dimethylpicolinate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
-5 °C

Procedure

77.4 ml 2 mol/L trimethylsilyldiazomethan in hexane was added to 5,6-dimethyl-pyridine-2-carboxylic acid in 150 mL methanol and 600 mL dichlormethane at −5° C. The reaction was stirred 0.5 h at −5° C. and then warm up to RT. The solvent was removed and the residue was purified by chromatography on Silica (cyclohexane 7: ethyl acetate 3) to give 12.8 g desired product.

Workup

  1. temperaturewarm up to RT
  2. customThe solvent was removed
  3. customthe residue was purified by chromatography on Silica (cyclohexane 7: ethyl acetate 3)

Sources & evidence

ORD record
ord-29872c803ca94393b7a73c4190002c4b
Source dataset
uspto-grants-2014_09
Patent number
US08822464B2

Reaction notes

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