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

HRID 271723

Reaction equation

HRID 271723 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-da48be0f9bcf45baa2a4c0e2d708a57a
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Linked notes

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