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

HRID 581163Notes

Reaction equation

HRID 581163 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]>CN(C=O)C.C1COCC1.O.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 3

HCID 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 4

HCID 962WaterSolventHCID 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 with water and extracted with 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. extractionextracted with EtOAc
  3. washThe EtOAc solution was washed with water, saturated NaCl solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-8e922b1c154f4b66a778b062940027a2
Source dataset
uspto-grants-1999_07
Patent number
US05919810

Reaction notes

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