Pyridine → HCID 86756585, compound

HRID 322886Notes

Reaction equation

HRID 322886 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:31]=O)=[C:13]([CH:30]=1)[O:14][CH:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:34][OH:35].N1C=CC=CC=1>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:31]=[N:34][OH:35])=[C:13]([CH:30]=1)[O:14][CH:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 23204236HCID 23204236, compound

Product 1

HCID 86756585HCID 86756585, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (RS)-4-(5-benzyloxy-2-formylphenoxy)-4-(2-methylphenyl)butanoate (0.49 g), hydroxylamine hydrochloride (0.1 g) and pyridine (0.1 g) in ethanol (10 mL) is heated at reflux for 1 hour. The solvent is then removed in vacuo and the residue is partitioned between water (50 mL) and ethyl acetate (50 mL). The aqueous layer is extracted with ethyl acetate (2×50 mL) and the combined organic extracts are washed with brine (50 mL), dried over magnesium sulphate and filtered and the solvent is removed in vacuo, to give a yellow oil. Flash chromatography on silica gel, eluting with a mixture of petroleum ether (b.p.40-60° C.) and ethyl acetate (7:1 v/v), gives ethyl (RS)-4-(5-benzyloxy-2-hydroxyiminomethylphenoxy)-4-(2-methylphenyl)butanoate (E:Z ratio 4:1), (0.24 g).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. customThe solvent is then removed in vacuo
  4. customthe residue is partitioned between water (50 mL) and ethyl acetate (50 mL)
  5. extractionThe aqueous layer is extracted with ethyl acetate (2×50 mL)
  6. washthe combined organic extracts are washed with brine (50 mL)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent is removed in vacuo
  10. customto give a yellow oil
  11. washFlash chromatography on silica gel, eluting with a mixture of petroleum ether (b.p.40-60° C.) and ethyl acetate (7:1 v/v)

Sources & evidence

ORD record
ord-72403f57c1794a598848d2b394c4e509
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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