Chlorotrimethylsilane → Methyl 2-(3-nitrophenyl)acetate
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
Product 1
Reagents, catalysts & solvents 1
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%).