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ChemicalBook CAS DataBase List 1H-INDOL-2-YLMETHANOL
24621-70-3

1H-INDOL-2-YLMETHANOL synthesis

7synthesis methods
Put 20kg of 4-oxoindole, 4kg of Pd/C catalyst with 5% Pd content (palladium carbon catalyst) and 60L of diethylene glycol dimethyl ether as solvent into a 100L reactor with stirring device, and then heat up the reactor with steam, turn on the stirring, an
-

Yield:24621-70-3 100%

Reaction Conditions:

Stage #1:2-carbethoxyindole with lithium aluminium tetrahydride in tetrahydrofuran at 0;
Stage #2: with water;sodium hydroxide in tetrahydrofuran

Steps:

6
Compound 17: (1H-indol-2-yl)methanolTo ethyl 1H-indole-2-carboxylate 16 (6.5 g, 34.35 mmol) in THF at 0° C. was added lithium aluminum hydride solution (1M, in THF 1.43 g, 37.78 mmol) dropwise and the reaction mixture was stirred for 3.5 hours at 0° C. The reaction mixture was quenched with H2O, 15% NaOH, and H2O before it was filtered and rinsed with THF. Reaction mixture was dried (anhydrous Na2SO4) and evaporation of the solvent gave 5.37 g (100% yield) of the crude (1H-indol-2-yl)methanol 17 which was used directly in the next step.

References:

Neosome Life Sciences, LLC US2012/302578, 2012, A1 Location in patent:Page/Page column 23

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