Indole → 1H-Indole-1-ethanol

HRID 1296636Notes

Reaction equation

HRID 1296636 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C1(=O)O[CH2:13][CH2:12][O:11]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.ClCCl>[N:1]1([CH2:13][CH2:12][OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 798IndoleHCID 7303Ethylene carbonateHCID 11430Potassium Carbonate

Product 1

HCID 137349961H-Indole-1-ethanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of indole (5.71 g, 48.7 mmol), ethylene carbonate (4.72 g, 53.6 mmol) and K2CO3 (6.73 g, 48.7 mmol) in DMF (20 mL) was heated under reflux for 2 h. The reaction mixture was diluted with dichloromethane, filtered, and concentrated in vacuo. The light brown oily residue was purified by chromatography on silica gel (13×6 cm) using n-hexane/ethyl acetate (1:1) as eluent. This gave 1.78 g (23%) of the title compound as a beige oil. HRMS m/z calcd for C10H11NO (M)+ 161.0841, found 161.0849. Anal. (C10H11NO.0.1H2O) C, H, N. *Previously described in a) J. Med. Chem. 1992, 35, 994-1001; b) ibid. 1998, 41, 1619-1630.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe light brown oily residue was purified by chromatography on silica gel (13×6 cm)

Sources & evidence

ORD record
ord-f0fc128007834335a34e52d8810df3be
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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