Water → 4-[[1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester

HRID 2256264Notes

Reaction equation

HRID 2256264 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]=[CH:5]2.[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CN(C=O)C.C1COCC1.CCOCC.CCCCCC>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:6]=[CH:5]2)[CH3:28]

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 107754621H-Indol-5-ol, 1-(phenylmethyl)-

Product 1

HCID 105930394-[[1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl esterYield 40.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 21584099Diethylether hexaneSolvent

Procedure

A solution of 850 mg (4.0 mmol) of 5-hydroxy-1-(phenylmethyl)-1H-indole in 75 mL of DMF and 20 mL of THF was treated with 200 mg (5.0 mmol) of 60% NaH/mineral oil and after stirring for 0.17 hours, 0.7 mL (4.9 mmol) of ethyl 4-bromobutyrate was added. After 2.75 hours, the mixture was diluted wish water and extracted wish EtOAc. The EtOAc solution was washed with water, saturated NaCl solution, dried(Na2SO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and the 545 mg (40% yield) of 4-[[1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester by eluting with a gradient, 15% ether/hexane→50% ether/hexane.

Workup

  1. waitAfter 2.75 hours
  2. additionthe mixture was diluted
  3. extractionextracted
  4. washThe EtOAc solution was washed with water, saturated NaCl solution, dried(Na2SO4)
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-f67106cb442349a9970a6369c07982d8
Source dataset
uspto-grants-1997_08
Patent number
US05654326

Reaction notes

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