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

HRID 2042936Notes

Reaction equation

HRID 2042936 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[CH:2]1.S(Cl)(Cl)=O.[CH3:18]O>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH3:18])=[O:12])=[CH:2]1

Participants

4

Reactant 3

HCID 802Indole-3-Acetic AcidHCID 887MethanolHCID 24386Thionyl Chloride

Product 1

HCID 74706Methyl indole-3-acetate

Procedure

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.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove solvent
  3. additionThe residue was diluted with EtOAc
  4. washwashed with aq. saturated NH4Cl solution, aq. saturated NaHCO3 solution and brine successively
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude titled compound 74 (10.9 g, quantitative) was used without further purification

Sources & evidence

ORD record
ord-cceab053345346b7ae93f93830353cc5
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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