Hydroxyamine hydrochloride → HCID 22175146, compound

HRID 49441Notes

Reaction equation

HRID 49441 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([CH3:15])=[CH:11][C:12](=O)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:17]O.C([O-])(=O)C.[Na+]>CO>[CH2:1]([CH:8]1[CH:13]=[C:12]([NH2:17])[CH:11]=[C:10]([CH3:15])[O:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 22175145HCID 22175145, compound

Product 1

HCID 22175146HCID 22175146, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This amine was prepared according to Scheme 32. To 0.37 g (1.8 mmol) of 2-benzyl-6-methyl-4-pyranone (G. Piancatilli, et. al., Synthesis, 1982, 248) was added 0.22 g (3.1 mmol) of hydroxylamine hydrochloride and 0.16 g (2 mmol) of sodium acetate in 10 mL of methanol. After stirring overnight, the mixture was partitioned between CH2Cl2 and water. The organic phase was dried and evaporated. The oily residue solidified upon standing at room temperature to give 0.4 g (99%) of the desired oxime 121 as a Z/E isomer mixture 1:1 by GC/MS with a molecular ion of 219, and that was used as is in the reduction reaction below.

Workup

  1. customthe mixture was partitioned between CH2Cl2 and water
  2. customThe organic phase was dried
  3. customevaporated
  4. customupon standing at room temperature

Sources & evidence

ORD record
ord-c9e380443e6d47f2bc65dbda49e343ed
Source dataset
uspto-grants-2004_03
Patent number
US06706740B2

Reaction notes

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