Trimethylsilyldiazomethane → Methyl 4-cyano-2-ethoxybenzoate

HRID 2263951Notes

Reaction equation

HRID 2263951 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:12][CH2:13][CH3:14])[CH:4]=1)#[N:2].[CH3:15][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[CH3:15][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[O:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 226750384-Cyano-2-ethoxybenzoic acid

Product 1

HCID 57809105Methyl 4-cyano-2-ethoxybenzoateYield 74%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

Crude 4-cyano-2-ethoxybenzoic acid (19 g) was dissolved in a mixture of benzene (446 mL) and methanol (111 mL). At 0° C., (trimethylsilyl)diazomethane (76 mL, 2.0 M in ether, Aldrich) was added slowly and then at room temperature. Solvent was removed, and the residue was purified by flash chromatography (silica gel, eluting with 25% ethyl acetate in hexane) to give 4-cyano-2-ethoxybenzoic acid methyl ester as a solid (15.5 g, 74%).

Workup

  1. customat room temperature
  2. customSolvent was removed
  3. customthe residue was purified by flash chromatography (silica gel, eluting with 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-37b04d8b9673454b98f31226cfaab574
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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