Water → [[2-ethyl-1-(2-phenyl-phenylmethyl)-1H-indol-4-yl]oxy]acetic acid tert-butyl ester

HRID 1280822Notes

Reaction equation

HRID 1280822 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].O>CN(C)C=O>[C:37]([O:36][C:34](=[O:35])[CH2:33][O:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:3]([CH2:1][CH3:2])[N:4]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:40])([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 106162052-ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indole

Product 1

HCID 53758830[[2-ethyl-1-(2-phenyl-phenylmethyl)-1H-indol-4-yl]oxy]acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indole (0.8 g, 0.00245 mol) was added to a slurry of cesium carbonate (0.98 g, 0.003 mol) in 15 mL of dimethylformamide, stirred at room temperature for ten minutes and then the t-butyl bromoacetate was added all at once. After stirring at room temperature overnight, the solution was poured into water and extracted in ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated to an oil that crystallized on standing at room temperature. This material was slurried in hexane and filtered to give 0.93 g of subtitled compound as a tan solid.

Workup

  1. stirringAfter stirring at room temperature overnight
  2. extractionextracted in ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil that
  7. customcrystallized
  8. customon standing at room temperature
  9. filtrationfiltered

Sources & evidence

ORD record
ord-0f60aad8d5db41bea22e89bd65f94e17
Source dataset
uspto-grants-2002_09
Patent number
US06451839B1

Reaction notes

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