Sodium Hydroxide → 1H-Pyrrole-2-carboxylic acid, 1-(2,3,3-triiodo-2-propenyl)-, methyl ester

HRID 1284547Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[I:10][C:11](=[C:24]([I:26])[I:25])[CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>CN(C)C=O>[I:10][C:11](=[C:24]([I:26])[I:25])[CH2:12][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of 125 mg (1 mmole) of methyl pyrrole-2-carboxylate in 5 ml of dry N,N-dimethylformamide were added 590 mg (1 mmole) of 2,3,3-triiodoallyl-p-toluenesulfonate and 50 mg (1.2 mmoles) of powdery sodium hydroxide while cooling at 10° C. and the resulting mixture was stirred for one hour. The reaction mixture was extracted with ethyl acetate and water, the ethyl acetate layer was separated, washed with water and then dried. The ethyl acetate layer was concentrated under reduced pressure, the residual oily substance was allowed to stand with 1.0 ml of methanol, thereby separating a crystalline substance, 1-(2',3',3'-triiodoallyl)-2-methoxycarbonylpyrrole. It was then recovered by filtration. Yield 127 mg (23% yield), mp 88°-90° C.

Workup

extractionThe reaction mixture was extracted with ethyl acetate and water
customthe ethyl acetate layer was separated
washwashed with water
customdried
concentrationThe ethyl acetate layer was concentrated under reduced pressure
customseparating a crystalline substance, 1-(2',3',3'-triiodoallyl)-2-methoxycarbonylpyrrole
filtrationIt was then recovered by filtration

Sources & evidence

ORD record: ord-c2ce03bbaf804a558c27a28d06bf56e0
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04563472

Reaction notes

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