3-Methylbutanal → HCID 59487372, compound

HRID 1099587Notes

Reaction equation

HRID 1099587 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6](=O)[C:7]([F:10])([F:9])[F:8])[CH3:2].CC1(C)O[C:18](=[O:20])[CH2:17][C:16](=O)O1.C([O-])(=O)C.[NH4+:27].[CH3:28][CH:29]([CH3:33])[CH2:30]C=O>C(O)(=O)C.C(OCC)(=O)C.O>[CH2:28]([CH:16]1[CH2:17][C:18](=[O:20])[NH:27][C:6]([C:7]([F:10])([F:9])[F:8])=[C:5]1[C:4]([O:3][CH2:1][CH3:2])=[O:12])[CH:29]([CH3:33])[CH3:30]

Participants

7

Reactant 4

HCID 115523-MethylbutanalHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 517165Ammonium Acetate2×

Product 1

HCID 59487372HCID 59487372, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 22728543Water ethylacetateSolvent

Procedure

2.00 g (23.2 mmol) of ethyl-4,4,4-trifluoro-3-oxobutanoate, 3.35 g (23.2 mmol) of 2,2-dimethyl-1,3-dioxane-4,6-dione and 1.97 g (25.5 mmol) of ammonium acetate were initially charged in 20 ml of acetic acid, and 2.49 ml (23.2 mmol) of 3-methylbutyraldehyde were added. The mixture was then stirred at reflux temperature overnight. After removal of the volatile components on a rotary evaporator, another 8.95 g (116.1 mmol) of ammonium acetate were added to the residue, and the mixture was stirred at 180° C. overnight. After cooling, the mixture was taken up in 200 ml of ethyl acetate/water (1/1), and the aqueous phase was extracted with ethyl acetate (2×). The combined organic phases were dried with magnesium sulfate and the solvent was removed on a rotary evaporator. Work-up was carried out by column chromatography (silica gel: cyclohexane/ethyl acetate=4/1). Drying under high vacuum gave 1.40 g (19% of theory) of the target compound.

Workup

  1. temperatureat reflux temperature overnight
  2. customAfter removal of the volatile components
  3. customon a rotary evaporator
  4. stirringthe mixture was stirred at 180° C. overnight
  5. temperatureAfter cooling
  6. extractionthe aqueous phase was extracted with ethyl acetate (2×)
  7. dry with materialThe combined organic phases were dried with magnesium sulfate
  8. customthe solvent was removed on a rotary evaporator
  9. customDrying under high vacuum
  10. customgave 1.40 g (19% of theory) of the target compound

Sources & evidence

ORD record
ord-8272d42e74564887b8a41cf5fc7a04fb
Source dataset
uspto-grants-2012_03
Patent number
US08143411B2

Reaction notes

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