2-(4-acetonylphenoxymethyl)-5-benzyloxy-4H-pyran-4-one → 2-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one

HRID 465437ノート

反応式

HRID 465437 の反応式
[CH2:1]([C:5]1[CH:27]=[CH:26][C:8]([O:9][CH2:10][C:11]2[O:12][CH:13]=[C:14]([O:18]CC3C=CC=CC=3)[C:15](=[O:17])[CH:16]=2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3]>CO>[CH2:1]([C:5]1[CH:27]=[CH:26][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:3]

参加物

3

反応物 1

HCID 198745522-(4-acetonylphenoxymethyl)-5-benzyloxy-4H-pyran-4-one

生成物 1

HCID 198745552-(4-acetonylphenoxymethyl)-5-hydroxy-4H-pyran-4-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 2-(4-acetonylphenoxymethyl)-5-benzyloxy-4H-pyran-4-one, ethylene ketal (2.0 g) in methanol was hydrogenated at ambient temperature and pressure over 10% palladium on carbon until absorption of hydrogen was complete. The catalyst was filtered off and the solvent removed in vacuo. The residue was dissolved in acetone (75 ml) and treated with 2N-hydrochloric acid solution (2 ml) and allowed to stand at room temperature for 2 h. The solvent was then removed in vacuo, 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 the solvent, the residue was purified by column chromatography on silica using methanol-chloroform (2:98) as eluent to give 2-(4-acetonylphenoxymethyl) -5-hydroxy-4H-pyran-4-one, (1.2 g).

後処理

  1. customwas hydrogenated at ambient temperature
  2. custompressure over 10% palladium on carbon until absorption of hydrogen
  3. filtrationThe catalyst was filtered off
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was dissolved in acetone (75 ml)
  6. additiontreated with 2N-hydrochloric acid solution (2 ml)
  7. customThe solvent was then removed in vacuo
  8. dissolutionthe residue dissolved in ethyl acetate
  9. washwashed with water (2×50 ml), brine (1×50 ml)
  10. dry with materialdried (magnesium sulphate)
  11. filtrationAfter filtration and evaporation of the solvent
  12. customthe residue was purified by column chromatography on silica

出典と根拠

ORDレコード
ord-c97613f8c4b04e17b5de7d84cd992bf7
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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