Hydroxyamine hydrochloride → 4,5-(Dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenal oxime

HRID 1741954Notes

Reaction equation

HRID 1741954 reaction equation
[CH3:1][C:2]1([CH3:17])[O:16][CH:13]([CH:14]=[CH2:15])[CH:4]([CH:5]([O:9][CH2:10][O:11][CH3:12])[CH2:6][CH:7]=O)[O:3]1.Cl.[NH2:19][OH:20]>N1C=CC=CC=1.C(OCC)C>[CH3:1][C:2]1([CH3:17])[O:16][CH:13]([CH:14]=[CH2:15])[CH:4]([CH:5]([O:9][CH2:10][O:11][CH3:12])[CH2:6][CH:7]=[N:19][OH:20])[O:3]1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 190109744,5-(Dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenal

Product 1

HCID 730980754,5-(Dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenal oximeYield 91.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

The above 4,5-(dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenal (91.9 mg) was dissolved in 1 ml of pyridine, and 45 mg of hydroxylamine hydrochloride was added at room temperature, and stirring was conducted at room temperature for 8 hours. The reaction mixture was diluted with diethyl ether. The diluted reaction mixture was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to afford 89.5 mg of 4,5-(dimethylmethylenedioxy)-3-methoxymethoxy-6-heptenal oxime having the following properties (yield 52%).

Workup

  1. customThe diluted reaction mixture
  2. washwas washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f2f5b48425ae4ee8a421f980258c31e4
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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