Trimethylsilyldiazomethane → Methyl 2-methoxy-4-nitrobenzeneacetate

HRID 2077771Notes

Reaction equation

HRID 2077771 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH2:12][C:13]([OH:15])=[O:14].[CH3:16][Si](C=[N+]=[N-])(C)C>CO.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 21875535415912-52-6

Product 1

HCID 21875908Methyl 2-methoxy-4-nitrobenzeneacetateYield 96.9%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2-(2-methoxy-4-nitrophenyl)acetic acid (step 2, 1.2 g, 5.5 mmol) in methanol/dichloromethane (11 ml, 1/1) was added trimethylsilyldiazomethane (2 M, 5.6 ml, 11.8 mmol) and stirred for 10 min at room temperature. The mixture was quenched with saturated citric acid aqueous solution and the extracted with ethyl acetate (3×20 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give 1.2 g of title compound as orange solid.

Workup

  1. customThe mixture was quenched with saturated citric acid aqueous solution
  2. extractionthe extracted with ethyl acetate (3×20 ml)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d02b1430e4804e0e903f9e677ad05c0c
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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