Iodoethane → HCID 13799993, compound

HRID 868208Notes

Reaction equation

HRID 868208 reaction equation
[OH:1][CH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:3].[CH2:23](I)[CH3:24].[OH-].[K+]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:23]([O:1][CH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:13]([C:16]1[CH:17]=[CH:18][C:19]([CH3:20])=[CH:21][CH:22]=1)(=[O:15])=[O:14])[CH3:3])[CH3:24]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 13799992HCID 13799992, compound

Product 1

HCID 13799993HCID 13799993, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

11.9 g (37.8 mmol) of 4-(1-hydroxyethyl)-1-tosyl indole in 150 ml of methylene chloride was mixed at room temperature under argon with 13.3 g (85 mmol) of ethyl iodide, 6.7 g of tetrabutylammonium hydrogen sulfate and 6.7 g (119.3 mmol) of pulverized potassium hydroxide one after the other. The solution was stirred for 2 hours. After filtration over silica gel, the solution was again mixed with equal amounts of ethyl iodide, tetrabutylammonium hydrogen sulfate and potassium hydrogen oxide. The reaction mixture was stirred for 2 hours at room temperature, washed with 200 ml of water and the organic phase dried, filtered and concentrated. Subsequent chromatography on silica gel with cyclohexane/ethyl acetate (8:2) yielded 8.5 g of 4-(1-ethoxyethyl)-1-tosyl indole as oil.

Workup

  1. filtrationAfter filtration over silica gel
  2. additionthe solution was again mixed with equal amounts of ethyl iodide, tetrabutylammonium hydrogen sulfate and potassium hydrogen oxide
  3. stirringThe reaction mixture was stirred for 2 hours at room temperature
  4. washwashed with 200 ml of water
  5. customthe organic phase dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4eca6e021b8646fa9b01d2fa6491128d
Source dataset
uspto-grants-1988_10
Patent number
US04778800

Reaction notes

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