5-Methyl-2-formylpyrrole → 4-benzyloxy-5-(5-methyl-1H-pyrrol-2-yl-methylene)-1,5-dihydro-pyrrol-2-one

HRID 840754Notes

Reaction equation

[CH:1]([C:3]1[NH:4][C:5]([CH3:8])=[CH:6][CH:7]=1)=O.[CH2:9]([O:16][C:17]1[CH2:21][NH:20][C:19](=[O:22])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O>[CH2:9]([O:16][C:17]1[C:21](=[CH:1][C:3]2[NH:4][C:5]([CH3:8])=[CH:6][CH:7]=2)[NH:20][C:19](=[O:22])[CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-formyl-5-methylpyrrole (4 g; 36.65 mmols) and 4-benzyloxy-3-pyrrolin-2-one (8.24 g; 43.78 mmols) in DMSO (65 ml) 2N sodium hydroxyde (45 ml) was added under nitrogen atmosphere and the mixture was stirred at 60° C. for 8 hours. After dilution with water (200 ml) the yellow suspension was filtered. The crude material was taken up in ethyl acetate, stirred and filtered to give 4-benzyloxy-5-(5-methyl-1H-pyrrol-2-yl-methylene)-1,5-dihydro-pyrrol-2-one (7.7 g; 27.49 mmols) as a 4:1 Z:E mixture. Yield: 75%

Workup

filtrationAfter dilution with water (200 ml) the yellow suspension was filtered
stirringstirred
filtrationfiltered

Sources & evidence

ORD record: ord-eeda2353b38e4bf19851b0d6256aef2a
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369096B1

Reaction notes

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