Diethyl Ether → 1-(1-Methyl-1H-indol-4-yl)-ethanol

HRID 2113127Notes

Reaction equation

HRID 2113127 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11](O)C)=C[CH:2]=1.CN1C2C=CC=[C:19]([CH:24]=[O:25])C=2C=C1.C[Mg]I.C(OCC)C>O1CCCC1>[CH3:2][N:1]1[C:10]2[C:5](=[C:6]([CH:24]([OH:25])[CH3:19])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:11]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 53147551-(Quinolin-4-yl)ethanolHCID 172211111-Methyl-1H-indole-4-carbaldehydeHCID 178418373HCID 178418373, compound

Product 1

HCID 223913981-(1-Methyl-1H-indol-4-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by the same procedure for 1-quinolin-4-yl-ethanol from 1-methyl-1H-indole-4-carbaldehyde (2.8 g, 17.6 mmol), 3 M methyl magnesium iodide solution in diethyl ether (10 mL, 30 mmol, Aldrich) and anhydrous tetrahydrofuran (20 mL). The crude title compound obtained in form as yellow oil in 97% yield (3.0 g, 17.1 mmol).

Sources & evidence

ORD record
ord-11b825e3332d403d9b10894be6599bc3
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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