Methyl 2-(2,3-dihydro-1H-indol-3-yl)acetate → 2-(2,3-Dihydro-1H-indol-3-yl)ethan-1-ol

HRID 1984000Notes

Reaction equation

HRID 1984000 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([CH2:10][C:11](OC)=[O:12])[CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([CH2:10][CH2:11][OH:12])[CH2:2]1

Participants

4

Reactant 2

HCID 11816349Methyl 2-(2,3-dihydro-1H-indol-3-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 230093562-(2,3-Dihydro-1H-indol-3-yl)ethan-1-olYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl (RS)-(2,3-Dihydro-1H-indol-3-yl)acetate (30.0 g, 0.16 mol) was dissolved in tetrahydrofuran (500 mL) and subsequently added to a suspension of lithium aluminium hydride (10.6 g, 0.28 mol) in tetrahydrofuran (500 mL) over a period of 75 min at 33-39° C. The reaction was quenched by sequential addition of water (20 mL), 15% NaOH (10 mL) and water (50 mL), and then MgSO4. The mixture was stirred at room temperature for 1 h, filtered and concentrated in vacuo to give the title compound (24.2 g, 95%).

Workup

  1. customThe reaction was quenched by sequential addition of water (20 mL), 15% NaOH (10 mL) and water (50 mL)
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b3a3d87a20d4c8eaf68c45bcf631317
Source dataset
uspto-grants-2009_06
Patent number
US07544685B2

Reaction notes

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