Iodoethane → 6-Ethoxy-1H-indole

HRID 2215828Notes

Reaction equation

HRID 2215828 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.[CH2:13](I)[CH3:14]>CN(C=O)C>[CH2:13]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)[CH3:14]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 5245086-Hydroxyindole

Product 1

HCID 5267696-Ethoxy-1H-indoleYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 1.65 g, 41 mmol) was added to a solution of 6-hydroxyindole (5.0 g, 38 mmol) in anhydrous DMF (25 mL) at −20° C. under N2. The resulting dark green solution was allowed to warm up to room temperature and stirred for 10 min. Ethyl iodide (3.3 mL, 6.4 g, 41 mmol) was added, and the resulting solution was stirred at room temperature for 1 h. The mixture was poured into ice-water (150 mL), and extracted with EtOAc (3×200 mL). The organic solution was dried (MgSO4) and concentrated at reduced pressure. The residue was purified by flash chromatography (SiO2, 5% then 15% EtOAc/hexanes) to give the title compound (4.5 g, 75%) as a white solid. 1H NMR (CDCl3) δ 7.98 (br. s, 1H), 7.50 (m, 1H), 7.10 (m, 1H), 6.90 (m, 1H), 6.80 (m, 1H), 6.45 (m, 1H), 4.10 (q, J=6.5 Hz, 2H), 1.45 (t, J=6.5 Hz, 3H).

Workup

  1. stirringthe resulting solution was stirred at room temperature for 1 h
  2. extractionextracted with EtOAc (3×200 mL)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by flash chromatography (SiO2, 5%

Sources & evidence

ORD record
ord-30d7d9fab5a1430c83ed5c9131f0e249
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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