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

HRID 1655062Notes

Reaction equation

HRID 1655062 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:11][C:12]([O:14][CH3:15])=[O:13]>>[CH3:15][O:14][C:12](=[O:13])[CH2:11][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

3

Reactant 2

HCID 798IndoleHCID 60984Methyl bromoacetate

Product 1

HCID 966836methyl 2-(1H-indol-1-yl)acetate

Procedure

This compound was prepared from indole and methyl bromoacetate by the method described in Example 10, part i. The reaction mixture was worked up by concentrating in vacuo, diluting with water and extracting with ethyl acetate (3x). The combined extracts were washed with water (3x) and brine, dried and evaporated to an oil. The residue was purified by chromatography on flash silica eluting with petroleum spirit 40°-60° C.--diethyl ether (5:1, 2:1) to give the product.

Workup

  1. concentrationby concentrating in vacuo
  2. additiondiluting with water
  3. extractionextracting with ethyl acetate (3x)
  4. washThe combined extracts were washed with water (3x) and brine
  5. customdried
  6. customevaporated to an oil
  7. customThe residue was purified by chromatography on flash silica eluting with petroleum spirit 40°-60° C.
  8. customdiethyl ether (5:1, 2:1) to give the product

Sources & evidence

ORD record
ord-ae578bbd2dcd4899a9911b36c06ae63a
Source dataset
uspto-grants-1995_04
Patent number
US05410061

Reaction notes

Loading…