Hydroxyamine hydrochloride → 4-Carbomethoxy-3-keto-2-propyl-tetrahydrothiophene oxime

HRID 2058539Notes

Reaction equation

HRID 2058539 reaction equation
[C:1]([CH:5]1[CH2:9][S:8][CH:7]([CH2:10][CH2:11][CH3:12])[C:6]1=O)([O:3][CH3:4])=[O:2].Cl.[NH2:15][OH:16]>N1C=CC=CC=1>[C:1]([CH:5]1[CH2:9][S:8][CH:7]([CH2:10][CH2:11][CH3:12])[C:6]1=[N:15][OH:16])([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 13286145Methyl 4-oxo-5-propylthiolane-3-carboxylate

Product 1

HCID 867382784-Carbomethoxy-3-keto-2-propyl-tetrahydrothiophene oximeYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 94.0 g (0.465 mole) of 4-carbomethoxy-3-keto-2-propyl-tetrahydrothiophene in 250 ml of dry pyridine was treated with 40.0 (0.576 mole) of hydroxylamine hydrochloride at 25°. The reaction was stirred overnight at room temperature. The solvent was evaporated and the residue was partitioned between 1 N HCl and methylene chloride. The organic phase was dried over sodium sulfate and evaporated to afford 100 g (0.461 mole, 99%) of pure 4-carbomethoxy-3-keto-2-propyl-tetrahydrothiophene oxime as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between 1 N HCl and methylene chloride
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-265ff9426a6c4a6089fa30dcdfb847aa
Source dataset
uspto-grants-1982_03
Patent number
US04317915

Reaction notes

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