Trimethylsilyldiazomethane → Methyl 4-cyano-2-ethoxybenzoate

HRID 2105831Notes

Reaction equation

HRID 2105831 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=1)#[N:9]>C1C=CC=CC=1.CO>[C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:16][CH3:1])=[O:15])=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=1)#[N:9]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 226750384-Cyano-2-ethoxybenzoic acid

Product 1

HCID 57809105Methyl 4-cyano-2-ethoxybenzoateYield 72.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

(Trimethylsilyl)diazomethane (2 M in hexanes, 1.47 mL, 2.93 mmol) was added to a solution of 4-cyano-2-ethoxybenzoic acid (280 mg, 1.47 mmol) in benzene (8.0 mL) and methanol (1.6 mL). The reaction was stirred for 1 h and then degassed with air for 30 min. Evaporation of the solvent and purification of the crude residue by flash column chromatography (silica gel, eluting with 0-20% ethyl acetate in hexanes) gave methyl 4-cyano-2-ethoxybenzoate as a yellow solid (218 mg, 71%).

Workup

  1. customdegassed with air for 30 min
  2. customEvaporation of the solvent and purification of the crude residue
  3. washby flash column chromatography (silica gel, eluting with 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-412f143d7b93495ba41db8c247a39c92
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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