2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-(4-Methylsulfonylbenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 526836Notes

Reaction equation

HRID 526836 reaction equation
N1CCC[C@H]1C(O)=O.[CH3:9][S:10]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)(=[O:12])=[O:11].[CH3:21][C:22]1([CH3:30])[O:29][C:27](=[O:28])[CH2:26][C:24](=[O:25])[O:23]1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>CCO>[CH3:9][S:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][CH:26]2[C:27](=[O:28])[O:29][C:22]([CH3:30])([CH3:21])[O:23][C:24]2=[O:25])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 70849Hantzsch esterHCID 145742L-ProlineHCID 2203764-(Methylsulfonyl)benzaldehyde

Product 1

HCID 867155855-(4-Methylsulfonylbenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Proline (0.126 g, 1.086 mmol) was added to a solution of 4-(methylsulfonyl)benzaldehyde (1.00 g, 5.43 mmol) and Meldrum's acid (1.38 g, 5.43 mmol) in EtOH (10 mL). The mixture was stirred at room temperature for 1 hour and then diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (1.38 g, 5.43 mmol) was added. Stirring was continued for 3 hours and then EtOH was removed under reduced pressure. The residue was diluted with i-PrOH and filtered to provide the title compound as a white solid.

Workup

  1. stirringStirring
  2. waitwas continued for 3 hours
  3. customEtOH was removed under reduced pressure
  4. additionThe residue was diluted with i-PrOH
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4e754d38806c4ddd877e3d8cfbdb617d
Source dataset
uspto-grants-2016_05
Patent number
US09346782B2

Reaction notes

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