Indole → 1H-Indole-1-ethanol

HRID 2223314Notes

Reaction equation

HRID 2223314 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].Br[CH:13]([OH:15])[CH3:14]>CS(C)=O>[OH:15][CH2:13][CH2:14][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 14797Potassium HydroxideHCID 14202443Ethanol, 1-bromo-

Product 1

HCID 137349961H-Indole-1-ethanolYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The intermediate product, reported in J. Med. Chem., 1998, 41/10, 1619-1639, was prepared according to the procedure described therein, with the exception of the duration of the reaction time (equal to 30 hours instead of 30 minutes), starting from indole (5.0 g, 42.7 mmol), KOH (3.6 g, 64.1 mmol) and bromoethanol (6.4 g, 51.3 mmol) in 50 ml of anhydrous DMSO, at a temperature of 25-30° C., to obtain 5 g of oily product (yield: 73%).

Workup

  1. custom, 1998, 41/10, 1619-1639, was prepared

Sources & evidence

ORD record
ord-71dec4448675466b88b9344eb09c368e
Source dataset
uspto-grants-2008_05
Patent number
US07375124B2

Reaction notes

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