Trifluoroacetic anhydride → ethyl 2-[(E)-2-phenylethenyl]-1,3-oxazole-4-carboxylate

HRID 546395

反応式

HRID 546395 の反応式
C(=O)([O-])O.[Na+].Br[CH2:7][C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:15]([NH2:25])(=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1.C(OCC)(=O)C>[CH2:12]([O:11][C:9]([C:8]1[N:25]=[C:15](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:24][CH:7]=1)=[O:10])[CH3:13]

参加物

7

反応物 4

HCID 9845Trifluoroacetic anhydrideHCID 121352-Propenamide, 3-phenyl-HCID 66144Ethyl bromopyruvateHCID 516892Sodium Bicarbonate2 回

生成物 1

HCID 5708074ethyl 2-[(E)-2-phenylethenyl]-1,3-oxazole-4-carboxylate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Synthesis was conducted in accordance with the report (J. Org. Chem., 1996, Vol. 61, p. 6496) by Panek et al. Sodium hydrogencarbonate (22.8 g) and ethyl bromopyruvate (10.5 ml) were added to a solution of cinnamamide (10.0 g) in tetrahydrofuran (250 ml) at room temperature, and the mixture was heated under reflux for 48 hours. The reaction mixture was allowed to cool to room temperature, filtered through Celite and then concentrated under reduced pressure to obtain residue. Trifluoroacetic anhydride (30 ml) was added to a solution of this residue in tetrahydrofuran (30 ml) at 0° C., and the mixture was gradually warmed to room temperature. After the mixture was stirred for 63 hours, a saturated aqueous solution (500 ml) of sodium hydrogencarbonate and ethyl acetate (150 ml) were added to the reaction mixture, and an organic layer was separated. The water layer was extracted with ethyl acetate (150 ml). The organic layers were combined, washed with saturated saline (150 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1→3:1) to obtain the title compound (10.9 g) as a colorless solid.

後処理

  1. customSynthesis
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 48 hours
  4. filtrationfiltered through Celite
  5. concentrationconcentrated under reduced pressure
  6. customto obtain residue
  7. temperaturethe mixture was gradually warmed to room temperature
  8. customan organic layer was separated
  9. extractionThe water layer was extracted with ethyl acetate (150 ml)
  10. washwashed with saturated saline (150 ml)
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1→3:1)

出典と根拠

ORDレコード
ord-7ac6df7d0dde443f97b5919e1dbaecd7
出典データセット
uspto-grants-2011_05
特許番号
US07935824B2

関連ノート

読み込み中…