2-Chloroethanol → 2-(5-Iodo-indol-1-yl)-ethanol

HRID 271723

Reaktionsgleichung

Reaktionsgleichung von HRID 271723
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].[K+].Cl[CH2:14][CH2:15][OH:16].CCOC(C)=O>CS(C)=O>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:14][CH2:15][OH:16])[CH:6]=[CH:5]2

Komponenten

6

Edukt 4

HCID 342-ChloroethanolHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 27823135-Iodo-1H-indole

Produkt 1

HCID 457893802-(5-Iodo-indol-1-yl)-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

Under an N2 atmosphere 30 g (121 mmol) 5-iodoindole are added to a suspension of 27.1 g (484 mmol) KOH in 150 mL DMSO. The reaction mixture is kept for 1 h at RT, cooled to 0° C. with ice water, 9.7 mL (145 mmol) of 2-chloroethanol in 30 mL DMSO are slowly added dropwise and stirred for 4.5 h at RT. The reaction mixture is combined with 1 L EtOAc, washed four times with in each case 800 mL water and once with 400 mL saturated NaCl solution and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc/EtOAc 3:1).

Aufarbeitung

  1. additionare slowly added dropwise
  2. washwashed four times with in each case 800 mL water
  3. dry with materialonce with 400 mL saturated NaCl solution and the organic phase is dried over Na2SO4
  4. customis purified by chromatography (silica gel, cyc/EtOAc 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-da48be0f9bcf45baa2a4c0e2d708a57a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452911B2

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