Hydroxyamine hydrochloride → Ethyl 5-pentyl-1,2-oxazole-3-carboxylate

HRID 1074132Notes

Reaction equation

HRID 1074132 reaction equation
[C:1]([CH2:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.[NH2:17]O.C(=O)([O-])O.[Na+]>C(O)C>[CH2:2]([C:1]1[O:7][N:17]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 12777406Ethyl 2,4-dioxononanoate

Product 1

HCID 12777407Ethyl 5-pentyl-1,2-oxazole-3-carboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 38 g of ethyl hexanoylpyruvate in 190 ml of ethanol in the presence of 14.4 g of hydroxylamine hydrochloride and 16 g of sodium hydrogencarbonate was heated under reflux for 3 hours. After the reaction mixture was cooled to room temperature, the insoluble materials were separated by filtration, and the remaining filtrate was concentrated. The resulting residue was dissolved in chloroform (500 ml), which was washed with water, concentrated to give 5-pentyl-3-carboethoxyisoxazole as a liquid (36 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customthe insoluble materials were separated by filtration
  4. concentrationthe remaining filtrate was concentrated
  5. dissolutionThe resulting residue was dissolved in chloroform (500 ml)
  6. washwhich was washed with water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-203de7a5936044bf9ff09e2773f294de
Source dataset
uspto-grants-1990_11
Patent number
US04973576

Reaction notes

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