Water → Methyl 3-(1H-indol-3-yl)propanoate

HRID 2389336Notes

Reaction equation

HRID 2389336 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1.[C:15]([O-])([O-])=O.[K+].[K+].IC.O>CC#N>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 37441H-Indole-3-propanoic acidHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 21711Methyl 3-(1H-indol-3-yl)propanoateYield 99.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of 3-(1H-indol-3-yl)propanoic acid (0.3 g) in MeCN (9 mL) was added K2CO3 (0.33 g) at ambient temperature followed by addition of iodomethane (0.15 mL). After 3 hours, water was added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified by column chromatography (n-hexane:EtOAc=3:1) to give methyl 3-(1H-indol-3-yl)propanoate (0.32 g).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography (n-hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-7ec54f6d13634de3b30f630aa7f20018
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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