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

HRID 1954229Notes

Reaction equation

HRID 1954229 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>O1CCCC1.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

7

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 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

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 tetrahydrofuran (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-56bd17f3932a4fc59593bad03ea0c4a0
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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