2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 58197305, compound

HRID 928794Notes

Reaction equation

HRID 928794 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([CH3:22])[O:21][C:19](=[O:20])[CH2:18][C:16](=[O:17])[O:15]1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O.N1CCC[C@H]1C(O)=O>CCO>[CH3:13][C:14]1([CH3:22])[O:21][C:19](=[O:20])[CH:18]([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=2)[C:16](=[O:17])[O:15]1

Participants

6

Reactant 4

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 70849Hantzsch esterHCID 145742L-Proline

Product 1

HCID 58197305HCID 58197305, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Similar procedures to those referenced in Tett. Lett. (2006), 651, D. Ramachary; Eur. J. Org. Chem. (2008), 975, D. Ramachary were employed. To a 5 L 3-necked flask fitted with an overhead mechanical stirrer was charged with 4-(trifluoromethyl)benzaldehyde (43.5 g, 250 mmol) followed by the addition of anhydrous EtOH (3,000 mL) and Meldrum's acid (37.5 g, 260 mmol), diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (67.5 g, 266 mmol) and lastly L-proline (6.0 g, 51 mmol) all at room temperature. The yellowish reaction mixture was stirred at room temperature under N2. An aliquot was removed after 4 hours and rinsed with EtOH and then Et2O, and air dried. The 1H NMR of this aliquot showed the reaction to be complete. The full reaction was stopped and the white precipitate from the reaction was collected by filtration and rinsed with EtOH and then Et2O and dried under vacuum to give the title compound in the first crop as a fine white solid. The yellowish mother liquors were concentrated and allowed to crystallize overnight from EtOH and the solid material was collected as before to provide the title compound.

Workup

  1. customTo a 5 L 3-necked flask fitted with an overhead mechanical stirrer
  2. customThe yellowish reaction mixture
  3. customAn aliquot was removed after 4 hours
  4. washrinsed with EtOH
  5. dry with materialEt2O, and air dried
  6. customthe reaction
  7. customThe full reaction
  8. filtrationthe white precipitate from the reaction was collected by filtration
  9. washrinsed with EtOH
  10. dry with materialEt2O and dried under vacuum

Sources & evidence

ORD record
ord-e6b70ce17b9d4df1a14e9209599eae70
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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