Sodium hydride → Benzyl 1-(ethoxycarbonylpentyl)-2-indolecarboxylate

HRID 844436Notes

Reaction equation

HRID 844436 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C=O)C>[CH2:31]([O:30][C:28]([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 7723355benzyl 1H-indole-2-carboxylate

Product 1

HCID 70161676Benzyl 1-(ethoxycarbonylpentyl)-2-indolecarboxylateYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture containing 3 g of benzyl 2-indolecarboxylate in 30 ml of anhydrous DMF and 500 mg of sodium hydride at 60% in oil is left stirring under a nitrogen atmosphere for 1 hour. 3 g of ethyl 6-bromohexanoate in 10 ml of DMF are added, at 0° C., and the mixture is left stirring overnight at RT. The solvents are evaporated off and the residue is taken up in EtOAc, washed with water, dried over MgSO4 and concentrated. The residue is chromatographed on a column of silica H, eluting with a heptane/toluene mixture (50/50; v/v) to give 4.17 g of the expected compound.

Workup

  1. waitis left
  2. waitthe mixture is left
  3. stirringstirring overnight at RT
  4. customThe solvents are evaporated off
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is chromatographed on a column of silica H
  9. washeluting with a heptane/toluene mixture (50/50; v/v)

Sources & evidence

ORD record
ord-90ffdc75111544aa81eed2d06cf4ec25
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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