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Triethylamine → 2,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dione

HRID 901331
Notes
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Reaction equation

HRID 901331 reaction equation
CO[C:3]1[CH2:4][CH2:5][CH2:6][N:7]=1.[C:8]1(=[O:17])[O:16][C:13]([CH3:15])([CH3:14])[O:12][C:10](=[O:11])[CH2:9]1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:14][C:13]1([CH3:15])[O:16][C:8](=[O:17])[C:9](=[C:3]2[CH2:4][CH2:5][CH2:6][NH:7]2)[C:10](=[O:11])[O:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 3534432-Methoxy-1-Pyrroline

Product 1

HCID 7085372,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dioneYield 71.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5-Methoxy-3,4-dihydro-2H-pyrrole (5.35 g, 54.0 mmol), isopropylidene malonate (7.78 g, 54.0 mmol), triethylamine (1.35 mL, 9.7 mmol) and benzene (55 mL) is refluxed under nitrogen overnight. The reaction is cooled to RT and concentrated and the crude product is recrystalized from EtOH (95 mL) to give the title compound as a white solid (8.13 g, 38.5 mmol). 1H NMR (CDCl3, 300 MHz) 3.73(t, 2H), 3.35(t, 2H), 2.20-2.08(m, 2H), 1.66(s, 6H).

Workup

  1. concentrationconcentrated
  2. customthe crude product is recrystalized from EtOH (95 mL)

Sources & evidence

ORD record
ord-5e7deb17ac814ff1907339b9a7fbd611
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07361663B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes