Ethyl propiolate → HCID 178491959, compound

HRID 744920Notes

Reaction equation

HRID 744920 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[C:11](OCC)(=[O:14])[C:12]#[CH:13].CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[OH:14][C:11]1[CH:12]=[CH:13][N:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1

Participants

6

Reactant 3

HCID 12182Ethyl propiolateHCID 77023(4-Methoxyphenyl)hydrazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 178491959HCID 178491959, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 72.7 g of 4-methoxyphenylhydrazine in 700 ml of tert-butanol was treated dropwise at 30° C. with 56.8 g of ethyl propiolate. A total of 118 g of potassium tert-butoxide was then introduced in portions with ice cooling into the mixture thus obtained. After 12 h at 25° C., the solvent was distilled off under reduced pressure and the residue thus obtained was taken up in water. The aqueous solution was washed with dichloromethane and then acidified with conc. acetic acid with cooling to a pH of 9, the product being deposited as a solid. After washing and drying, 60.3 g of the title compound (60% of theory) were obtained; m.p.: 167°-170° C.

Workup

  1. customthus obtained
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue thus obtained
  4. washThe aqueous solution was washed with dichloromethane
  5. temperaturewith cooling to a pH of 9
  6. washAfter washing
  7. customdrying

Sources & evidence

ORD record
ord-886608cc1cfa45e79aa704a9ea0cb711
Source dataset
uspto-grants-1996_09
Patent number
US05559244

Reaction notes

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