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

HRID 1250166Notes

Reaction equation

HRID 1250166 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, 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. filtrationfiltered
  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-bf92406e9062447abf25e27ac16248af
Source dataset
uspto-grants-2002_01
Patent number
US06337336B1

Reaction notes

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