Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Al+3].[Cl-].[Cl-].[Cl-].[N+](C)([O-])=O.[CH3:20][O:21]C(Cl)Cl>ClCCCl>[CH:20]([C:5]1[CH:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:2]([CH3:1])[CH:6]=1)=[O:21]Participants
6
Conditions
- Temperature
- -30 °C
Procedure
Ethyl 1-methyl-1H-pyrrole-2-carboxylate (3.69 g, 28.24 mmol; see step (ii) above) and AlCl3 (8.02 g, 60.11 mmol) were added to a solution of nitromethane (40 mL), and 1,2-dichloroethane (40 mL) at −30° C. Dichloromethyl methyl ether (2.5 mL, 28 mmol) in 1,2-dichloroethane (10 mL) was added rapidly to the solution and the mixture was allowed to stir at −30° C. for 16 h. The solution was then poured onto ice (50 g) and the layers were separated. The aqueous layer was then extracted with ether (50 mL). The combined organic fractions were dried (MgSO4), filtered and the solvent removed under reduced pressure, to yield the title compound as a crystalline brown/black solid (4.77 g, 94%).
Workup
- additionThe solution was then poured onto ice (50 g)
- customthe layers were separated
- extractionThe aqueous layer was then extracted with ether (50 mL)
- dry with materialThe combined organic fractions were dried (MgSO4)
- filtrationfiltered
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-204e22db0e294236aebe7163257327ac
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012967B2
Linked notes
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