Methyl 2-(1-methyl-1H-indol-3-yl)acetate → 2-(1-methyl-1H-indol-3-yl)ethan-1-ol

HRID 1031496Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18](OC)=[O:19])=[CH:9]1>O1CCCC1>[OH:19][CH2:18][CH2:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([CH3:7])[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of LiAlH4 (2.0 g, 0.052 mol) in 50 mL of dry tetrahydrofuran was added dropwise a solution of methyl 1-methylindole-3-acetate (5.25 g, 0.026 mol) in 70 mL of dry tetrahyqrofuran at -10° C. under Ar. The mixture was refluxed for 1 h and then it was cooled at 0° C. and quenched by the sequential addition of 2 mL of H2O, 2 mL of 15% aqueous NaOH and finally 6 mL of H2O. The resulting slurry was filtered and the filter cake was washed with additional tetrahydrofuran. Evaporation of the filtrate gave the product (40 g, 89%) as an oil which was used without further purification.

Workup

temperatureThe mixture was refluxed for 1 h
customquenched by the sequential addition of 2 mL of H2O, 2 mL of 15% aqueous NaOH and finally 6 mL of H2O
filtrationThe resulting slurry was filtered
washthe filter cake was washed with additional tetrahydrofuran
customEvaporation of the filtrate

Sources & evidence

ORD record: ord-a578c95886894db4bfb6f0a295f271a4
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04954502

Reaction notes

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