Methyl acetoacetate → HCID 2854420, compound

HRID 734743Notes

Reaction equation

HRID 734743 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]1(C)[O:17]C(=O)CC(=O)O1.C([O-])(=O)C.[NH4+:25].O=[C:27]([CH3:33])[CH2:28][C:29]([O:31][CH3:32])=[O:30]>C(O)(=O)C.CO.CCOC(C)=O.O>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]1[CH2:11][C:12](=[O:17])[NH:25][C:27]([CH3:33])=[C:28]1[C:29]([O:31][CH3:32])=[O:30]

Participants

8

Reactant 4

HCID 7757Methyl acetoacetateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 737702,4-DifluorobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 2854420HCID 2854420, compoundYield 32.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
110 °C

Procedure

2,4-Difluorobenzaldehyde (3.28 mL, 30 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (4.32 g, 30 mmol), ammonium acetate (2.46 g, 32 mmol), and methyl 3-oxobutanoate (3.23 mL, 30 mmol) were combined in acetic acid (30 mL) under nitrogen. This mixture was heated to 110° C. for 1 h. The reaction mixture was cooled to room temperature and then poured into water (100 mL). The mixture was decanted to leave yellow oil and white solid, which was taken up in MeOH/EtOAc and then concentrated. The residue was triturated with 5% ether/hexanes to afford the title compound (2.72 g, 32%). MS (ES+) m/e 282 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe mixture was decanted
  3. customto leave yellow oil and white solid, which
  4. concentrationconcentrated
  5. customThe residue was triturated with 5% ether/hexanes

Sources & evidence

ORD record
ord-413609dcea114c5c912785516cfe6ac4
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

Loading…