Ethyl Acetate → HCID 53909511, compound

HRID 486062Notes

Reaction equation

HRID 486062 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[NH:5][C:4]=1[CH2:14][CH2:15][CH3:16])[CH3:2].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)(=O)C.Br>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[NH:5][C:4]=1[CH2:14][CH2:15][CH3:16])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 19097339HCID 19097339, compound

Product 1

HCID 53909511HCID 53909511, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

3-Ethyl-5-methoxy-2-propyl indole (2.92 g) in 15 ml of hydrogen bromide acetic acid solution was heated at 100° C. for 4 hours. The cooled solution was poured into an aqueous sodium bicarbonate solution (100 ml) and ethyl acetate with stirring. The separated organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The crude product was chromatographed on silica gel using 30% ethyl acetate in n-hexanes as eluent to yield 3-ethyl-5-hydroxy-2-propyl indole (2.7 g).

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was chromatographed on silica gel using 30% ethyl acetate in n-hexanes as eluent

Sources & evidence

ORD record
ord-be1364ea0d074675ac990b494bfe3819
Source dataset
uspto-grants-1994_03
Patent number
US05290788

Reaction notes

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