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Water → Ethyl 1-methyl-4-[(E)-2-(3-quinolinyl)ethenyl]-1H-pyrrole-2-carboxylate

HRID 907377
Notes
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Reaction equation

HRID 907377 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11]P(=O)([O-])[O-])[CH:2]=1.[H-].[Na+].[CH:18]([C:20]1[CH:21]=[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:23]([CH3:25])[CH:24]=1)=O.O>C1COCC1>[CH3:25][N:23]1[CH:24]=[C:20](/[CH:18]=[CH:11]/[C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:21]=[C:22]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 14643811Ethyl 4-formyl-1-methyl-1H-pyrrole-2-carboxylateHCID 866381023-Quinolinylmethylphosphonate

Product 1

HCID 67392785Ethyl 1-methyl-4-[(E)-2-(3-quinolinyl)ethenyl]-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

3-Quinolinylmethylphosphonate (0.503 g, 1.93 mmol; see step (iii) above) was dissolved in anhydrous THF (2 mL) and NaH (0.273 g, 11.37 mmol) was then added in small portions to the solution and the resulting mixture was then aged for an additional 10 min. Ethyl 4-formyl-1-methyl-1H-pyrrole-2-carboxylate (0.313 g, 1.92 mmol; see Preparation 11 above) in anhydrous THF (3 mL) was added dropwise and the solution allowed to stir for 16 h. Water (5 mL) was added to the mixture (dropwise initially) during which time the sub-title compound precipitated as a yellow solid (0.201 g, 34%).

Sources & evidence

ORD record
ord-a3f9bbab02e5434083abe9aabad66fed
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08012967B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes