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

HRID 1507298Notes

Reaction equation

HRID 1507298 reaction equation
N1CCC[C@H]1C(O)=O.[F: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>[F: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 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 680234-FluorobenzaldehydeHCID 70849Hantzsch esterHCID 145742L-Proline

Product 1

HCID 860963525-(4-Fluorobenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Proline (5.748 g, 49.42 mmol) was added to a solution of 4-fluorobenzaldehyde (24.99 g, 197.3 mmol) and Meldrum's acid (29.01 g, 197.3 mmol) in EtOH (900 mL). The mixture was stirred at room temperature for 1.5 hours, then diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (50.99 g, 197.3 mmol) was added along with an additional 100 mL of EtOH. The mixture was stirred overnight and EtOH was removed under reduced pressure. The residue was triturated with i-PrOH and filtered to provide the title compound as a white solid.

Workup

  1. stirringThe mixture was stirred overnight
  2. customEtOH was removed under reduced pressure
  3. customThe residue was triturated with i-PrOH
  4. filtrationfiltered

Sources & evidence

ORD record
ord-59059c1ae3954c3e85d33e851c6c2f4b
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

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