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Ethyl bromoacetate → 4-(1-tert-Butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid ethyl ester

HRID 412549
Notes
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Reaction equation

HRID 412549 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[H-].[Na+]>O1CCCC1>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][O:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH:10]2[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]2)=[CH:15][CH:16]=1)[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 185363684-(1-Tert-butoxycarbonylpyrrolidin-3-yloxy)phenol

Product 1

HCID 600642154-(1-tert-Butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)phenol (2.14 g) in tetrahydrofuran (43 l) were added ethyl bromoacetate (1.1 ml) and 60% sodium hydride (368 mg) with ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, ice water was added and the mixture was extracted with ethyl acetate and washed with 10% aqueous citric acid solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) and dried under reduced pressure to give the title compound (2.605 g).

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with 10% aqueous citric acid solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-2dc3a6af6251494ab08f78521a6ce33a
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06562828B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes