Sodium Hydroxide → Methyl 1-[2-(2-tetrahydropyranyl)oxyethyl]-2-indolecarboxylate

HRID 1067757Notes

Reaction equation

HRID 1067757 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].[OH-].[Na+].I[CH2:17][CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1>CN(C)C=O>[O:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH:20]1[O:19][CH2:18][CH2:17][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70992Methyl 1H-indole-2-carboxylateHCID 111186622H-Pyran, tetrahydro-2-(2-iodoethoxy)-

Product 1

HCID 21194121Methyl 1-[2-(2-tetrahydropyranyl)oxyethyl]-2-indolecarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction was carried out in a manner similar to Reference Example 5 except for using 2.0 g (11.4 mmol) of methyl 2-indolecarboxylate, 0.55 g (13.7 mmol) of 60% sodium hydroxide, 3.63 g (13.7 mmol) of 2-(2-iodo-ethoxy)tetrahydropyran (prepared from 2-iodoethanol and 3,4-dihydro-2H-pyran) and 50 ml of dimethylformamide. Thus, 2.87 g (83.0%) of methyl 1-[2-(2-tetrahydro-pyranyl)oxyethyl]-2-indolecarboxylate was obtained.

Sources & evidence

ORD record
ord-0edb686bd6734f4384906e9a8a815c31
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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