Chlorotrimethylsilane → Methyl 2-(3-nitrophenyl)acetate

HRID 2373615Notes

Reaction equation

HRID 2373615 reaction equation
[CH3:1][Si](Cl)(C)C.[N+:6]([C:9]1[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7]>CO>[N+:6]([C:9]1[CH:10]=[C:11]([CH2:15][C:16]([O:18][CH3:1])=[O:17])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 158763-Nitrophenylacetic acid

Product 1

HCID 526967Methyl 2-(3-nitrophenyl)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethylsilyl chloride (5.6 mL, 2.0 equiv.) was added to a stirred solution of (3-nitrophenyl)acetic acid (4.0 g) in methanol (60 ml). The resulting solution was stirred at room temperature for 18 hours, then concentrated at reduced pressure and partitioned between DCM and aqueous sodium hydrogencarbonate solution. The organic phase was dried over sodium sulfate, filtered and concentrated under vacuum to give the title compound as a colourless liquid (4.2 g, 100%).

Workup

  1. concentrationconcentrated at reduced pressure
  2. custompartitioned between DCM and aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2e00ff4feb9d40bc810ce6f1e123afc9
Source dataset
uspto-grants-2008_12
Patent number
US07459456B2

Reaction notes

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