4-Chlorobenzaldehyde → 5-(4-Chlorobenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 928712Notes

Reaction equation

HRID 928712 reaction equation
N1CCC[C@H]1C(O)=O.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.[CH3:18][C:19]1([CH3:27])[O:26][C:24](=[O:25])[CH2:23][C:21](=[O:22])[O:20]1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>CCO>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][CH:23]2[C:24](=[O:25])[O:26][C:19]([CH3:27])([CH3:18])[O:20][C:21]2=[O:22])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 70849Hantzsch esterHCID 145742L-Proline

Product 1

HCID 108801105-(4-Chlorobenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Proline (0.165 g, 1.42 mmol) was added to a solution of 4-chlorobenzaldehyde (1.00 g, 7.11 mmol) and Meldrum's acid (1.03 g, 7.11 mmol) in EtOH (10 mL). The mixture was stirred at room temperature for 1 hour and diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (1.80 g, 7.11 mmol) was added. Stirring was continued for 3 hours and EtOH removed under reduced pressure. The residue was diluted with i-PrOH and filtered to provide the desired compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-731056ea565043e58135b47f2e993128
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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