Ethyl Acetoacetate → HCID 178429254, compound

HRID 1764060Notes

Reaction equation

HRID 1764060 reaction equation
[C:1]([O:7]CC)(=O)[CH2:2][C:3]([CH3:5])=O.C(O)(=O)C(O)=O.[CH:16]1([NH:22][NH2:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(O)C>[CH:16]1([N:22]2[C:1]([OH:7])=[CH:2][C:3]([CH3:5])=[N:23]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 22769939CYCLOHEXYLHYDRAZINE OXALATE

Product 1

HCID 178429254HCID 178429254, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl acetoacetate (26 g) and cyclohexylhydrazine oxalate (40 g) in ethanol (100 ml) was heated at sufficient temperature and in a manner to allow removal of the ethanol by distillation. The temperature was gradually raised to about 130°, and heating was continued at this temperature for 4 hours, during which time by-product water and additional ethanol were continuously removed by distillation. The reaction mixture, after cooling to room temperature, was dissolved in methylene chloride and extracted with a saturated solution of sodium bicarbonate. The methylene chloride layer was dried and concentrated to give a viscous residue, which was induced to crystallize upon trituration with diethyl ether. The solid was collected to give 2-cyclohexyl-3-hydroxy-5-methylpyrazole (16.5 g), m.p. 153°. The assigned structure of the product as consistent with its infrared spectrum.

Workup

  1. customremoval of the ethanol
  2. distillationby distillation
  3. temperatureThe temperature was gradually raised to about 130°
  4. temperatureheating
  5. customwere continuously removed by distillation
  6. dissolutionwas dissolved in methylene chloride
  7. extractionextracted with a saturated solution of sodium bicarbonate
  8. dry with materialThe methylene chloride layer was dried
  9. concentrationconcentrated
  10. customto give a viscous residue, which
  11. customto crystallize upon trituration with diethyl ether
  12. customThe solid was collected

Sources & evidence

ORD record
ord-d4186ac9b18945a68b48acecd174e5f4
Source dataset
uspto-grants-1978_09
Patent number
US04115096

Reaction notes

Loading…