Water → HCID 69886411, compound

HRID 1883151Notes

Reaction equation

HRID 1883151 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH3:4].[CH3:23]I.O>CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69885427HCID 69885427, compound

Product 1

HCID 69886411HCID 69886411, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.11 g, 4 mmol) and anhydrous DMF (2 mL) was added a solution of 1-[2-(2-Hydroxy-ethoxy)-ethyl]-1H-indole-2-carboxylic acid ethyl ester (0.64 g, 2.3 mmol) in anhydrous DMF (5 mL). The reaction was allowed to stir at room temperature then was added methyl iodide (0.15 mL, 2.4 mmol). The reaction was allowed to stir for an additional 5.5 hours and then was poured onto 50 mL water and extracted with three 50 mL portions of ethyl acetate. The combined organics were washed with three 50 mL portions of water, dried on sodium sulfate, and concentrated. Purification by column chromatography (25:75 ethyl acetate:hexane) gave 1-[2-(2-Methoxy-ethoxy)ethyl]-1H-indole-2-carboxylic acid ethyl ester.

Workup

  1. stirringto stir for an additional 5.5 hours
  2. extractionextracted with three 50 mL portions of ethyl acetate
  3. washThe combined organics were washed with three 50 mL portions of water
  4. customdried on sodium sulfate
  5. concentrationconcentrated
  6. customPurification by column chromatography (25:75 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-cfc4889a3fad4a57a23390f4ed1d38a1
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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