Chloromethyl Methyl Ether → 4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile

HRID 1582930Notes

Reaction equation

[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]#[N:12].[CH3:13][O:14]CCl>[N+](C)([O-])=O.ClCCl.ClCCl>[C:11]([C:7]1[N:6]([CH3:5])[CH:10]=[C:9]([CH:13]=[O:14])[CH:8]=1)#[N:12]

Participants

Conditions

Temperature: -20 °C

Procedure

Aluminum trichloride (24.24 g, 180.86 mmol) was dissolved in nitromethane/dichloromethane (1/1, 320 ml), the solution was cooled to −20° C., and 1-methylpyrrole-2-carbonitrile (8 g, 75.36 mmol) was added. α,α-Dichlorodimethyl ether (10.4 g, 90.43 mmol), dissolved in dichloromethane (42 ml), was subsequently added dropwise. After stirring for 4 h at 0° C., the batch was poured onto ice (200 g). The aqueous phase was extracted with diethyl ether. The combined organic phases were washed until neutral with saturated sodium hydrogen carbonate solution, water and saturated sodium chloride solution. After drying over sodium sulfate, the solvent was removed in a rotary evaporator. The crude product was employed in the reactions below without further purification.

Workup

additionwas subsequently added dropwise
additionthe batch was poured onto ice (200 g)
extractionThe aqueous phase was extracted with diethyl ether
washThe combined organic phases were washed until neutral with saturated sodium hydrogen carbonate solution, water and saturated sodium chloride solution
dry with materialAfter drying over sodium sulfate
customthe solvent was removed in a rotary evaporator
customThe crude product was employed in the reactions below without further purification

Sources & evidence

ORD record: ord-e35ec4fc01264404830f81183dde9f0e
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740647B1

Reaction notes

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