Water → 5-(3-Oxo-1-phenylbutyl)-4-phenyl-2-oxo-4-oxazoline

HRID 47922

反応式

HRID 47922 の反応式
[C:1]1([C:7]2[NH:8][C:9](=[O:12])[O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13](=[CH:20][C:21](=[O:23])[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CS(O)(=O)=O.O>C(#N)C.C(OCC)(=O)C>[O:23]=[C:21]([CH3:22])[CH2:20][CH:13]([C:11]1[O:10][C:9](=[O:12])[NH:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 159094-Phenyl-3-Buten-2-oneHCID 1186694-Oxazolin-2-one, 4-phenyl-

生成物 1

HCID 155417565-(3-Oxo-1-phenylbutyl)-4-phenyl-2-oxo-4-oxazoline収率 86.3%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Phenyl-2-oxo-4-oxazoline (1.61 g) and benzalacetone (1.46 g) were dissolved in acetonitrile (20 mL), and methanesulfonic acid (0.96 mL) was added. The obtained mixture was stirred at room temperature for 1 h and water (100 mL) and ethyl acetate (100 mL) were added to the reaction mixture. The organic layer was separated, washed twice with water (50 mL), and concentrated under reduced pressure to give an oily substance. The obtained oily substance was subjected to silica gel column chromatography and eluted with n-hexane-ethyl acetate (1:1). The solvent was evaporated and isopropyl ether (50 mL) was added to the obtained oily substance to allow crystallization and the mixture was stirred at room temperature for 1 h. The crystals were collected by filtration and washed with isopropyl ether (20 mL) to give the title compound (2.65 g; yield 86.3%) as white crystals.

後処理

  1. customThe organic layer was separated
  2. washwashed twice with water (50 mL)
  3. concentrationconcentrated under reduced pressure
  4. customto give an oily substance
  5. washeluted with n-hexane-ethyl acetate (1:1)
  6. customThe solvent was evaporated
  7. additionisopropyl ether (50 mL) was added to the obtained oily substance
  8. customcrystallization
  9. stirringthe mixture was stirred at room temperature for 1 h
  10. filtrationThe crystals were collected by filtration
  11. washwashed with isopropyl ether (20 mL)

出典と根拠

ORDレコード
ord-5040fe76ccd14a1ba39324277a555368
出典データセット
uspto-grants-2004_03
特許番号
US06699995B1

関連ノート

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