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

HRID 465437노트

반응식

HRID 465437 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c97613f8c4b04e17b5de7d84cd992bf7
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153210

반응 노트

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