Methyl acetoacetate → HCID 2854419, compound

HRID 734669Notes

Reaction equation

HRID 734669 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:13][C:14]1(C)[O:19]C(=O)CC(=O)O1.[C:23]([O:29][CH3:30])(=[O:28])[CH2:24][C:25]([CH3:27])=O.C([O-])(=O)C.[NH4+:35]>C(O)(=O)C.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[CH2:13][C:14](=[O:19])[NH:35][C:25]([CH3:27])=[C:24]2[C:23]([O:29][CH3:30])=[O:28])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 2854419HCID 2854419, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-Trifluoromethylbenzaldehyde (25.0 mL, 147 mmol, 1.00 equiv), 2,2-dimethyl-1,3-dioxane-4,6-dione (21.2 g, 147 mmol, 1.00 equiv), methyl acetoacetate (15.8 mL, 147 mmol, 1.00 equiv), and ammonium acetate (11.8 g, 154 mmol, 1.05 equiv) were dissolved in acetic acid (150 mL) and heated to reflux for 2 hours. Addition of water to the stirred reaction mixture induced precipitation of a solid residue. The solid was recovered by filtration and triturated with 50% CH2Cl2/hexane to afford 8.50 g (19%) of the product as a white solid. MS (ES+) m/e 300 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customto the stirred reaction mixture
  4. customprecipitation of a solid residue
  5. filtrationThe solid was recovered by filtration
  6. customtriturated with 50% CH2Cl2/hexane

Sources & evidence

ORD record
ord-f9cc52b153244b81b4e7313c3cc4ee68
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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