Hydroxyamine hydrochloride → Ethyl 5-cyclopropylisoxazole-4-carboxylate

HRID 477498Notes

Reaction equation

HRID 477498 reaction equation
Cl.[NH2:2]O.[CH:4]1([C:7](=[O:18])[C:8](=[CH:14]OCC)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5]1>C(O)C>[CH:4]1([C:7]2[O:18][N:2]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 57004106Ethyl beta-cyclopropyl-alpha-ethoxymethylene-beta-ketopropionate

Product 1

HCID 14819891Ethyl 5-cyclopropylisoxazole-4-carboxylateYield 57.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of hydroxylamine hydrochloride (105.0 g. 1.51 mole), ethyl β-cyclopropyl-α-ethoxymethylene-β-ketopropionate (320.0 g., 1.51 mole) [prepared in Step A], and 1200 ml of ethanol was refluxed for 2 h. The solvent was removed in vacuo and the residue was partitioned between water and ether. The organic phase was separated, washed again with water, dried and evaporated to leave a dark, greasy solid. Trituration of the crude product under Skellysolve B gave 158 g of the title compound.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and ether
  4. customThe organic phase was separated
  5. washwashed again with water
  6. customdried
  7. customevaporated
  8. customto leave a dark, greasy solid

Sources & evidence

ORD record
ord-b46eb75938c34802a26c55248182ff4b
Source dataset
uspto-grants-1989_12
Patent number
US04888357

Reaction notes

Loading…