Ethyl indole-2-carboxylate → (1H-indol-2-yl)methanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:16](OCC)=[O:17]>O1CCCC1>[OH:17][CH2:16][C:8]1[NH:7][C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A suspension of lithium aluminum hydride (2.0 g, 0.20 mol) in tetrahydrofuran (100 mL) was cooled with stirring to 0° C. under nitrogen. A solution of ethyl indole-2-carboxylate (10.0 g, 0.052 mol) in tetrahydrofuran was added dropwise, maintaining the reaction temperature between 0°-5° C. After 1 h, the reaction was quenched with saturated sodium potassium tartrate solution. The reaction was filtered and the filter cake washed well with tetrahydrofuran. The tetrahydrofuran was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate solution was washed with water, saturated brine, dried over magnesium sulfate, filtered and freed of solvent. The title compound was obtained as a yellowish solid. NMR (CDCl3): δ8.18 (1H, bs), 7.57 (1H, d, J=8 Hz), 7.35 (1H, d, J=8 Hz), 7.26 (1H, s), 7.18 (1H, dt, J=1, 8 Hz), 7.10 (1H, dt, J=1, 8 Hz), 6.41 (1H, bs), 4.84 (2H, s).
Workup
- temperaturewas cooled
- temperaturemaintaining the reaction temperature between 0°-5° C
- customthe reaction was quenched with saturated sodium potassium tartrate solution
- filtrationThe reaction was filtered
- washthe filter cake washed well with tetrahydrofuran
- customThe tetrahydrofuran was evaporated in vacuo
- customthe residue partitioned between ethyl acetate and water
- washThe ethyl acetate solution was washed with water, saturated brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-4ae1f84f3c5a4a108ec76d8f91ce1329
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05124327
Reaction notes
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