Methyl acetoacetate → HCID 68829653, compound

HRID 734739Notes

Reaction equation

HRID 734739 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][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]>O.C(O)(=O)C>[F:1][C:2]1[C:9]([F:10])=[CH:8][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

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 1376642,3-DifluorobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 68829653HCID 68829653, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 2,3-difluorobenzaldehyde (2.23 mL, 20 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (2.88 g, 20 mmol) and ammonium acetate (1.62 g, 21 mmol) under nitrogen was added methyl 3-oxobutanoate (2.16 mL, 20 mmol) and acetic acid (20 mL). This mixture was then heated to 110° C. for 1 h. The reaction mixture was cooled to room temperature and then poured into water (80 mL). The mixture was decanted to leave a yellow oil, which was then triturated with 5% ether/hexanes to afford the title compound (1.89 g, 34%). 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 a yellow oil, which
  4. customwas then triturated with 5% ether/hexanes

Sources & evidence

ORD record
ord-dbba643e120644d3a33dfff4375ee529
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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