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

HRID 373385Notes

Reaction equation

HRID 373385 reaction equation
[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

Participants

7

Reactant 4

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

Product 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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f978c6f55b0b4cddaa5dc9e87b88c2d1
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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