Iodoethane → 7-ethoxy-1H-indole

HRID 2402680Notes

Reaction equation

HRID 2402680 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[OH:10])[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH3:19]>CC(C)=O>[CH2:18]([O:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2)[CH3:19]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27376517-Hydroxyindole

Product 1

HCID 198489347-ethoxy-1H-indole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1H-indol-7-ol (500 mg, 3.75 mmol) in acetone (10 mL) at r.t. was added potassium carbonate (3.11 g, 22.5 mmol), followed by iodoethane (0.45 mL, 5.63 mol). The mixture was stirred at r.t for 16 h then solvent removed under reduced pressure. The crude product thus obtained was purified by chromatography over silica gel to afford 7-ethoxy-1H-indole: 1H NMR (400 MHz, MeOD) δ ppm 1.51 (t, J=6.95 Hz, 3H), 4.22 (q, J=6.91 Hz, 2H), 6.42 (d, J=3.03 Hz, 1H), 6.63 (d, J=7.58 Hz, 1H), 6.92 (t, J=7.83 Hz, 1H), 7.04-7.23 (m, 2H); MS (ES+): m/z 162.20 (MH+).

Workup

  1. customsolvent removed under reduced pressure
  2. customThe crude product thus obtained
  3. customwas purified by chromatography over silica gel

Sources & evidence

ORD record
ord-9ad2193057f34a77b97dd93b850d90b3
Source dataset
uspto-grants-2014_08
Patent number
US08796455B2

Reaction notes

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