Ethyl Acetoacetate → HCID 86626592, compound

HRID 1011980Notes

Reaction equation

HRID 1011980 reaction equation
C([O-])C.[Na+].[C:5]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:6][C:7]([CH3:9])=O.[F:14][C:15]([F:41])([F:40])[C:16]1[CH:17]=[C:18]([NH:22][N:23]=[C:24](OS(C2C=CC(C)=CC=2)(=O)=O)[C:25]([F:28])([F:27])[F:26])[CH:19]=[CH:20][CH:21]=1>C(O)C.CCOC(C)=O>[CH2:12]([O:11][C:5]([C:6]1[C:24]([C:25]([F:26])([F:27])[F:28])=[N:23][N:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:40])([F:41])[F:14])[CH:17]=2)[C:7]=1[CH3:9])=[O:10])[CH3:13]

Participants

6

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 2723922Sodium ethoxideHCID 86626593HCID 86626593, compound

Product 1

HCID 86626592HCID 86626592, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium ethanolate 21% (in ethanol, 0.75 ml, 2 mmol) was added to ethyl acetoacetate (0.25 ml, 1.97 mmol) in 3 ml ethanol at 0° C. After 1 h at 0° C., a solution of (2Z or E)-1-[3-(trifluoromethyl)phenyl]-2-(2,2,2-trifluoro-1-{[(4-methylphenyl)sulfonyl]-oxy}ethylidene)hydrazine (254 mg, 0.60 mmol) in 5 ml ethanol was added. Stirring was continued for 18 h at room temperature and then the yellow solution was diluted with EtOAc washed with water and brine. The combined organic layers were dried over magnesium sulfate and evaporated. Column chromatography (EtOAc:n-heptane 1:3) delivered the title compound as light yellow solid (107 mg, 48%). MS: 367.3 (MH+).

Workup

  1. waitwas continued for 18 h at room temperature
  2. washwashed with water and brine
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-4be757c3bfbc4fddb7b3bf1113eb4ae8
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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