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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
ノート
印刷プレビュー

反応式

HRID 2215218 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒

1
HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7c6af5fcfc264114a8fa41104e72993c
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07109225B2

反応ノート

読み込み中…

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