Ethyl bromoacetate → (3-Formyl-indol-1-yl)-acetic acid ethyl ester

HRID 1360999Notes

Reaction equation

HRID 1360999 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=[O:2].[H-].[Na+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C)C=O>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([CH:1]=[O:2])=[CH:4]1)[CH3:20]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 801676(3-Formyl-indol-1-yl)-acetic acid ethyl esterYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Formylindol (10 g, 69 mmol) was dissolved in N,N-dimethylformamide (100 mL) and under an atmosphere of nitrogen and with external cooling, keeping the temperature below 15° C., sodium hydride (60% in mineral oil, 3.0 g, 76 mmol) was added in portions. Then a solution of ethyl bromoacetate (8.4 mL, 76 mmol) in N,N-dimethylformamide (15 mL) was added dropwise over 30 minutes and the resulting mixture was stirred at room temperature for 16 hours. The mixture was concentrated in vacuo and the residue was partitioned between water (300 mL) and ethyl acetate (2×150 mL). The combined organic extracts were washed with a saturated aqueous solution of ammonium chloride (100 mL), dried (MgSO4) and concentrated in vacuo to afford 15.9 g (quant.) of (3-formylindol-1-yl)acetic acid ethyl ester as an oil.

Workup

  1. additionwas added in portions
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between water (300 mL) and ethyl acetate (2×150 mL)
  4. washThe combined organic extracts were washed with a saturated aqueous solution of ammonium chloride (100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2d84d489e944ea28c858c9b53e9d954
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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