Indole-3-Acetic Acid → Methyl indole-3-acetate

Participants

Reaction Steps

To a solution of carboxylic acid 73 (10 g, 57.1 mmol) in MeOH (500 mL) was added dropwise thionyl chloride (21 mL, 285 mmol) at 0° C. The mixture was stirred at room temperature for 2 h and concentrated in vacuo to remove solvent. The residue was diluted with EtOAc and washed with aq. saturated NH4Cl solution, aq. saturated NaHCO3 solution and brine successively. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude titled compound 74 (10.9 g, quantitative) was used without further purification. MH+190.

Provenance & Evidence