Benzyl Bromide → 1h-Indole-3-acetic acid,1-(phenylmethyl)-,ethyl ester

HRID 1417422Notes

Reaction equation

HRID 1417422 reaction equation
[H-].[Na+].C([CH:5]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:6]([OH:8])=[O:7])C.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:26](OCC)(=O)[CH3:27].CCCCCC>CN(C)C=O>[CH2:18]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([CH2:5][C:6]([O:8][CH2:26][CH3:27])=[O:7])=[CH:10]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 122300802-(1H-indol-3-yl)butanoic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 109024521h-Indole-3-acetic acid,1-(phenylmethyl)-,ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Combine sodium hydride (1.08 g, 60% in oil, 27.1 mmol) and dimethylformamide (50 mL). Add a solution of ethyl indol-3-yl-acetic acid (5 g, 24.6 mmol) in dimethylformamide (20 mL). Stir until gas evolution ceases. Add benzyl bromide (5.85 mL, 49.2 mmol). Warm to ambient temperature. After 48 hours, partition the reaction mixture between ethyl acetate and water. Separate the organic layer and extract with a saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10% ethyl acetate/hexane to give the title compound.

Workup

  1. custompartition the reaction mixture between ethyl acetate and water
  2. customSeparate the organic layer
  3. extractionextract with a saturated sodium chloride solution
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-a4028f25337242e28d08a85db22a4177
Source dataset
uspto-grants-1999_03
Patent number
US05877202

Reaction notes

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