Trimethylsilyldiazomethane → Methyl 5,6-dimethylpicolinate

HRID 400443Notes

Reaction equation

HRID 400443 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

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. and the reaction was stirred for 0.5 h. After warming to RT the solvent was removed and the residue was purified by chromatorgaphie on Silica (cyclohexane/ethyl acetate:7/3) to give 12.8 g of the desired product.

Workup

  1. customwas removed
  2. customthe residue was purified by chromatorgaphie on Silica (cyclohexane/ethyl acetate:7/3)

Sources & evidence

ORD record
ord-7b8b139eed6a4409b40aeb9f7e844021
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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