Chromanone → 4H-1-Benzopyran-4-one, 2,3-dihydro-, oxime

HRID 896244Notes

Reaction equation

HRID 896244 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3][CH2:2]1.Cl.[NH2:13][OH:14].CC([O-])=O.[Na+]>C(O)C>[OH:14][N:13]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 68110ChromanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 44866984H-1-Benzopyran-4-one, 2,3-dihydro-, oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chromanone (5 g, 33.7 mmol), hydroxylamine hydrochloride (2.34 g, 33.7 mmol and NaOAc (2.766 g, 33.7 mmol) in 100 mL of ethanol was refluxed for 18 h. After cooling to RT, the solvent was removed and the residue was partitioned between water and EtOAc. The EtOAc layer was dried (MgSO4), and the solvent was removed. The solid obtained was triturated with hexane and filtered to provide 4.1 g of 4-hydroxyiminochroman.

Workup

  1. temperaturewas refluxed for 18 h
  2. customthe solvent was removed
  3. customthe residue was partitioned between water and EtOAc
  4. dry with materialThe EtOAc layer was dried (MgSO4)
  5. customthe solvent was removed
  6. customThe solid obtained
  7. customwas triturated with hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1ccdf92c6c6c42129c52c94e19c1a7a5
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

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