2-Chloroethanol → 4-(2-chloroethoxy)-1H-indole

HRID 1596776Notes

Reaction equation

HRID 1596776 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[Cl:11][CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[NH:6]1[C:7]2[C:3](=[C:2]([O:1][CH2:13][CH2:12][Cl:11])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 11776TriphenylphosphineHCID 754211H-indol-4-olHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 106317214-(2-chloroethoxy)-1H-indoleYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxyindole (4 g, 30 mmol), 2-chloroethanol (4.83 g, 60 mmol), triphenylphosphine (15.7 g, 60 mmol) in anhydrous tetrahydroufuran (40 ml) was slowly added diisopropyl azodicarboxylate (12.1 g, 60 mmol). The reaction was allowed to stir for 2.5 hours at room temperature, then poured into methylene chloride (250 ml), washed with water (3×100 ml) and dried over anhydrous sodium sulfate. This material was filtered and the solvent was removed under vacuum. Chromatography (20% hexanes-ethyl acetate) to remove triphenylphosphine, (20% methylene chloride-hexanes) afforded 2.94 g (50%) of product as a white solid: mp 69.5-72° C.

Workup

  1. washwashed with water (3×100 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThis material was filtered
  4. customthe solvent was removed under vacuum
  5. customChromatography (20% hexanes-ethyl acetate) to remove triphenylphosphine, (20% methylene chloride-hexanes)

Sources & evidence

ORD record
ord-41c527911bbe4206aa6852e499d83252
Source dataset
uspto-grants-2001_09
Patent number
US06291683B1

Reaction notes

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