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

HRID 1952859Notes

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) and, after cooling to -20° C., 1-methylpyrrole-2-carbonitrile (8 g, 75.36 mmol) was added. Then α,α-dichlorodimethyl ether (10.4 g, 90.43 mmol) dissolved in dichloromethane (42 ml) was added dropwise. After the mixture had been stirred at 0° C. for 4 h, it was poured onto ice (200 g). The aqueous phase was extracted with diethyl ether. The combined organic phases were washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution until neutral. After drying over sodium sulfate, the solvent was removed in a rotary evaporator. The crude product was employed without further purification in the following reactions. Yield: 9.2 g (91%).

Workup

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

Sources & evidence

ORD record: ord-101102c10d7f4da48ce0678c8325cfaf
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06114358

Reaction notes

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