2-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one → 2-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

HRID 465416ノート

反応式

HRID 465416 の反応式
[CH2:1]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][C:11]2[O:12][CH:13]=[C:14]([OH:18])[C:15](=[O:17])[CH:16]=2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=O.C(=O)(O)O.[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]([OH:35])[CH2:33][NH2:34])[CH:29]=[CH:30][CH:31]=1>C1C=CC=CC=1>[Cl:25][C:26]1[CH:27]=[C:28]([CH:29]=[CH:30][CH:31]=1)[CH:32]([OH:35])[CH2:33][NH:34][CH:2]([CH3:4])[CH2:1][C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][C:11]2[O:12][CH:13]=[C:14]([OH:18])[C:15](=[O:17])[CH:16]=2)=[CH:7][CH:6]=1

参加物

4

反応物 2

HCID 198745552-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-oneHCID 678659382-(3-Chlorophenyl)-2-hydroxyethylamine carbonate

生成物 1

HCID 198745272-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one収率 10.5%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A solution of 2-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one (0.7 g) and 2-(3-chlorophenyl)-2-hydroxyethylamine carbonate 0.52 g in benzene was heated under reflux for 2.5 h using a Dean and Stark head. The reaction mixture was allowed to cool and the solvent removed in vacuo. The residue was taken up in methanol, treated with sodium cyanoborohydride (0.2 g) and stirred at ambient temperature for 18 h. The solvent was evaporated under reduced pressure, the residue dissolved in ethyl acetate, washed with water (2×50 ml), brine(1×50 ml) and dried (magnesium sulphate). After filtration and evaporation of solvent the residue was purified by column chromatography on silica using methanol:chloroform (3:97) as eluent, followed by crystallisation from acetone to give 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one, (0.1 g), as a (35:65) mixture of diastereoisomers.

後処理

  1. temperatureunder reflux for 2.5 h
  2. temperatureto cool
  3. customthe solvent removed in vacuo
  4. additiontreated with sodium cyanoborohydride (0.2 g)
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionthe residue dissolved in ethyl acetate
  7. washwashed with water (2×50 ml), brine(1×50 ml)
  8. dry with materialdried (magnesium sulphate)
  9. filtrationAfter filtration and evaporation of solvent the residue
  10. customwas purified by column chromatography on silica
  11. customfollowed by crystallisation from acetone

出典と根拠

ORDレコード
ord-1df474a9044944edaf069ecfc3e51a7e
出典データセット
uspto-grants-1992_10
特許番号
US05153210

反応ノート

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