2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 86715583, compound

HRID 928721Notes

Reaction equation

HRID 928721 reaction equation
N1CCC[C@H]1C(O)=O.[N:9]1([C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[N:10]1.[CH3:22][C:23]1([CH3:31])[O:28][C:27](=[O:29])[CH2:26][C:25](=[O:30])[O:24]1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>C(O)C.C(O)(C)C>[N:9]1([C:14]2[CH:21]=[CH:20][C:17]([CH2:18][CH:26]3[C:27](=[O:29])[O:28][C:23]([CH3:31])([CH3:22])[O:24][C:25]3=[O:30])=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[N:10]1

Participants

7

Reactant 4

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 70849Hantzsch esterHCID 145742L-ProlineHCID 27764774-(1H-Pyrazol-1-yl)benzaldehyde

Product 1

HCID 86715583HCID 86715583, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3776IsopropanolSolvent

Procedure

L-Proline (4.07 g, 35.0 mmol) was added to a semi-heterogeneous mixture of 4-(1H-pyrazol-1-yl)benzaldehyde (30.0 g, 174 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (25.6 g, 174 mmol) in ethanol (996 mL) at room temperature. After 40 minutes, diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (44.1 g, 174 mmol) was added in one portion followed by ethanol (125 mL). After overnight stirring, the mixture was concentrated under reduced pressure to afford a yellow solid. Isopropanol (300 mL) was added and the heterogeneous mixture was sonicated for 30 minutes. The mixture was filtered and the filter cake was washed with isopropanol. The solids were collected and dried under vacuum to provide the title compound as a white solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto afford a yellow solid
  3. customthe heterogeneous mixture was sonicated for 30 minutes
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with isopropanol
  6. customThe solids were collected
  7. customdried under vacuum

Sources & evidence

ORD record
ord-148d5d4ee2fe42849eb8128857c5daa1
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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