Acetone → 2-(4-acetonylphenoxymethyl)-5-benzyloxy-4H-pyran-4-one ethylene ketal

HRID 465436ノート

反応式

HRID 465436 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH2:12]([O:19][C:20]1[C:21](=[O:28])[CH:22]=[C:23]([CH2:26]Cl)[O:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:35][C:36](C)=[O:37]>>[CH2:35]1[O:28][C:21]2([C:20]([O:19][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:25][O:24][C:23]([CH2:26][O:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][C:9]([CH3:10])=[O:11])=[CH:6][CH:7]=3)=[CH:22]2)[O:37][CH2:36]1

参加物

5

反応物 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 37033215-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-oneHCID 70192744-Hydroxyphenylacetone

生成物 1

HCID 572178562-(4-acetonylphenoxymethyl)-5-benzyloxy-4H-pyran-4-one ethylene ketal

実験手順

A mixture of 4-hydroxyphenylpropan-2-one, ethylene ketal (3.88 g), 5-benzyloxy-2-chloromethyl-4H-pyran-4-one (5.0 g) and potassium carbonate 3.5 g) in acetone, was heated under reflux for 18 h. The reaction mixture was cooled, filtered and the solvent removed in vacuo. The residue was dissolved in ethyl acetate, washed with 2N-sodium hydroxide solution (1×50 ml), water (2×50 ml), dried (magnesium sulphate), filtered and evaporated to dryness in vacuo. The residue was purified by column chromatography on silica using chloroform as eluent, followed by crystallisation from acetone to give 2-(4-acetonylphenoxymethyl)-5-benzyloxy-4H-pyran-4-one ethylene ketal, (5.3 g).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with 2N-sodium hydroxide solution (1×50 ml), water (2×50 ml)
  8. dry with materialdried (magnesium sulphate)
  9. filtrationfiltered
  10. customevaporated to dryness in vacuo
  11. customThe residue was purified by column chromatography on silica
  12. customfollowed by crystallisation from acetone

出典と根拠

ORDレコード
ord-4a7eaea6af364feea87a658a778a9858
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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