Trimethylsilyldiazomethane → Methyl 2-(4-hydroxy-3-nitrophenyl)acetate

HRID 1372593Notes

Reaction equation

HRID 1372593 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:15])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 4473644-Hydroxy-3-nitrophenylacetic acid

Product 1

HCID 1473109Methyl 2-(4-hydroxy-3-nitrophenyl)acetate

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

In methanol/toluene (1:10, 55 ml) was dissolved 4-hydroxy-3-nitrophenylacetic acid (2.0 g, 10.1 mmol). Trimethylsilyldiazomethane (2.0M hexane solution, 5.0 ml) was added dropwise to the resulting solution. After stirring at room temperature for 50 minutes, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was diluted with ethyl acetate. The ethyl acetate extract was then washed with a saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (2.15 g, 100%) was obtained as a yellow solid (this compound was provided for the subsequent reaction without further purification).

Workup

  1. distillationthe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. additionThe residue was diluted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas then washed with a saturated aqueous solution of sodium bicarbonate and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent, whereby the title compound (2.15 g, 100%)
  9. customwas obtained as a yellow solid (this compound
  10. customwas provided for the subsequent reaction without further purification)

Sources & evidence

ORD record
ord-73b1448e95f64a499ae4c838dd4bee96
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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