Acetylacetone → HCID 13607934, compound

HRID 1981594Notes

Reaction equation

HRID 1981594 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[C:13]([CH2:16][C:17](=[O:19])[CH3:18])(=O)[CH3:14].[NH2:20]/[C:21](/[CH3:28])=[CH:22]\[C:23]([O:25][CH2:26][CH3:27])=[O:24]>N1CCCCC1.C1(C)C=CC=CC=1>[CH2:26]([O:25][C:23]([C:22]1[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:4]=2)[C:16]([C:17](=[O:19])[CH3:18])=[C:13]([CH3:14])[NH:20][C:21]=1[CH3:28])=[O:24])[CH3:27]

Participants

6

Reactant 3

HCID 31261AcetylacetoneHCID 679903-(Trifluoromethyl)benzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Product 1

HCID 13607934HCID 13607934, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-trifluoromethylbenzaldehyde (12 g), acetylacetone (6.9 g), and piperidine (15 drops) was stirred at room temperature overnight. The reaction mixture was dissolved in toluene, and the toluene solution was washed with dilute hydrochloric acid, and dried over magnesium sulfate. Evaporation of toluene afforded a thick oily residue. Ethyl 3-aminocrotonate (7.0 g) was added to the residue, and the resulting mixture was heated on a steam bath overnight. The crude product was purified by a preparative HPLC, then recrystallized from toluene to give the titled product (4.1 g), mp 133°-1314.5° C.

Workup

  1. washthe toluene solution was washed with dilute hydrochloric acid
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of toluene
  4. customafforded a thick oily residue
  5. temperaturethe resulting mixture was heated on a steam bath overnight
  6. customThe crude product was purified by a preparative HPLC
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-6efe5a60fdd0434d872e762c8bd2a8bd
Source dataset
uspto-grants-1986_06
Patent number
US04593100

Reaction notes

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