Indole → methyl 2-(1H-indol-1-yl)acetate

HRID 346797Notes

Reaction equation

HRID 346797 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH3:12][O:13][C:14](=[O:17])[CH2:15]Br.O>CN(C=O)C>[CH3:12][O:13][C:14](=[O:17])[CH2:15][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 966836methyl 2-(1H-indol-1-yl)acetateYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (0.6 g, 15.0 mmol.) was added, while cooling with ice, to a solution of indole (1.17 g, 10.0 mmol.) and bromoacetic acid methyl ester (1.43 ml, 15 mmol.) in DMF. (20 ml), and stirring was carried out for 24 h at RT. For working up, water (50 ml) was added to the mixture, and extraction was carried out with EE (5×20 ml). The combined extracts were dried, filtered and concentrated. Chromatography with EE/cyclohexane (1:7) yielded 1.17 g of indol-1-yl-acetic acid methyl ester in the form of a colourless oil. These 1.17 g (6.18 mmol.) were dissolved in abs. methanol (100 ml); KOH (382 mg, 6.8 mmol.) was added and the mixture was heated at reflux for 2 h. For working up, the mixture was concentrated, water (20 ml) was added to the residue, the pH was adjusted to 4 with 1M HCl and the resulting solid was filtered off with suction. Indol-1-ylacetic acid was obtained in a yield of 0.96 g (white solid, m.p. 128–130° C.).

Workup

  1. customThe combined extracts were dried
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d022289b0f53439195171784d8057304
Source dataset
uspto-grants-2007_02
Patent number
US07173045B2

Reaction notes

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