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Potassium Iodide → [Rac]-3-[4-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxy)-2-methyl-phenyl]-2-ethoxy-propionic acid ethyl ester

HRID 2215218
Notes
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Reaction equation

HRID 2215218 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:14])[CH3:2].[C:19]([C:23]1[O:24][C:25]([CH3:30])=[C:26]([CH2:28]Cl)[N:27]=1)([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:28][C:26]2[N:27]=[C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])[O:24][C:25]=2[CH3:30])=[CH:9][C:8]=1[CH3:14])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 219495892-Tert-butyl-4-chloromethyl-5-methyl-oxazoleHCID 57792490[Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 69490107[Rac]-3-[4-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxy)-2-methyl-phenyl]-2-ethoxy-propionic acid ethyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of [rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (50 mg, 0.2 mmol), 2-tert-butyl-4-chloromethyl-5-methyl-oxazole (41 mg, 0.22 mmol, example 1, step b]), cesium carbonate (71 mg, 0.22 mmol) and a trace of potassium iodide were suspended in acetone (5 ml). The suspension was heated under reflux for 14 h, the solvent evaporated under reduced pressure and the residue dissolved in 2 N HCl/ice water 1/1 and ethyl acetate. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed two times with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, cyclohexane/AcOEt) to give 50 mg (0.12 mmol, 63%) of the title compound as colorless oil.

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 14 h
  3. customthe solvent evaporated under reduced pressure
  4. dissolutionthe residue dissolved in 2 N HCl/ice water 1/1
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted two times with ethyl acetate
  7. washThe combined organic layers were washed two times with brine
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe residue purified by column chromatography (silica gel, cyclohexane/AcOEt)

Sources & evidence

ORD record
ord-7c6af5fcfc264114a8fa41104e72993c
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07109225B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes