Water → (Z)-7-(4-fluorophenyl)-7-(2-hydroxy-5-hydroxyiminomethyl-3,4,6-trimethylphenyl)heptanoic acid

HRID 373385ノート

反応式

HRID 373385 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:22]([OH:23])=[C:21]([CH3:24])[C:20]([CH3:25])=[C:19]([CH:26]=O)[C:18]=2[CH3:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:35][OH:36].O>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:18]([CH3:28])=[C:19](/[CH:26]=[N:35]\[OH:36])[C:20]([CH3:25])=[C:21]([CH3:24])[C:22]=2[OH:23])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:18]([CH3:28])=[C:19](/[CH:26]=[N:35]/[OH:36])[C:20]([CH3:25])=[C:21]([CH3:24])[C:22]=2[OH:23])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 151251387-(4-Fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid

生成物 2

HCID 136403404(Z)-7-(4-fluorophenyl)-7-(2-hydroxy-5-hydroxyiminomethyl-3,4,6-trimethylphenyl)heptanoic acidHCID 136403405(E)-7-(4-fluorophenyl)-7-(2-hydroxy-5-hydroxyiminomethyl-3,4,6-trimethylphenyl)heptanoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution 7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid (1.3 g) in ethanol (13 ml) were added sodium acetate (1.3 g), hydroxylamine hydrochloride (0.26 g) and water (2.6 ml) and the mixture was refluxed for 4 hours. The solvent was distilled off under reduced pressure. To the residue were added water and 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to obtain (Z)-7-(4-fluorophenyl)-7-(2-hydroxy-5-hydroxyiminomethyl-3,4,6-trimethylphenyl)heptanoic acid (0.55 g) and (E)-7-(4-fluorophenyl)-7-(2-hydroxy-5-hydroxyiminomethyl-3,4,6-trimethylphenyl)heptanoic acid (0.75 g) (Compounds 47 and 48). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

後処理

  1. temperaturethe mixture was refluxed for 4 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionTo the residue were added water and 1N hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated saline
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-f978c6f55b0b4cddaa5dc9e87b88c2d1
出典データセット
uspto-grants-1992_11
特許番号
US05162571

反応ノート

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