2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-(Benzo[b]thiophen-2-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 926507Notes

Reaction equation

HRID 926507 reaction equation
N1CCC[C@H]1C(O)=O.[S:9]1[C:13]([CH:14]=O)=[CH:12][C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]1=2.[CH3:20][C:21]1([CH3:29])[O:28][C:26](=[O:27])[CH2:25][C:23](=[O:24])[O:22]1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>CCO>[S:9]1[C:13]([CH2:14][CH:25]2[C:26](=[O:27])[O:28][C:21]([CH3:29])([CH3:20])[O:22][C:23]2=[O:24])=[CH:12][C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]1=2

Participants

6

Reactant 4

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 70849Hantzsch esterHCID 145742L-ProlineHCID 7365001-Benzothiophene-2-carbaldehyde

Product 1

HCID 867155895-(Benzo[b]thiophen-2-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Proline (0.695 g, 5.98 mmol) was added to a solution of benzo[b]thiophene-2-carbaldehyde (5.00 g, 29.9 mmol) and Meldrum's acid (4.31 g, 29.9 mmol) in EtOH (50 mL). The mixture was stirred at room temperature for 1 hour and diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (7.57 g, 29.9 mmol) was added. Stirring was continued for 5 hours at room temperature and the precipitated product isolated by filtration rinsing further with iPrOH and dried under reduced pressure to provide the title compound as a white solid.

Workup

  1. stirringStirring
  2. waitwas continued for 5 hours at room temperature
  3. customthe precipitated product isolated by filtration
  4. washrinsing further with iPrOH
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-27cb75e38c5d479c9240a185085cf1a3
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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