4-methoxy-2,5-dihydro-1H-pyrrol-2-one → HCID 54158360, compound

HRID 1457271Notes

Reaction equation

HRID 1457271 reaction equation
[CH:1]([C:3]1[NH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][CH:7]=1)=O.[CH3:19][O:20][C:21]1[CH2:25][NH:24][C:23](=[O:26])[CH:22]=1>CS(C)=O>[CH3:19][O:20][C:21]1[C:25](=[CH:1][C:3]2[NH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][CH:7]=2)[NH:24][C:23](=[O:26])[CH:22]=1

Participants

4

Reactant 2

HCID 5747694-methoxy-2,5-dihydro-1H-pyrrol-2-oneHCID 108578682-formyl-5-undecylpyrrole

Product 1

HCID 54158360HCID 54158360, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-formyl-5-undecylpyrrole (4 g; 16.03 mmols) and 4-methoxy-3-pyrrolin-2-one (3.63 g; 32.06 mmols) in DMSO (53 ml) 2N sodium hydroxyde (45 ml) is added under nitrogen atmosphere and the mixture is stirred at 60° C. for 8 hours. After dilution with water (200 ml) the yellow suspension is extracted with dichloromethane (600 ml). The organic phase is shacked with water and brine, anhydrified over anhydrous sodium sulphate and evaporated to dryness. The crude material is taken up in hexane and filtered to give 4-methoxy-5-(5-undecyl-1H-pyrrol-2-yl-methylene)-1,5-dihydro-pyrrol-2-one (4.86 g; 14.11 mmols) as a yellow crystalline solid. Yield: 88%.

Workup

  1. extractionAfter dilution with water (200 ml) the yellow suspension is extracted with dichloromethane (600 ml)
  2. customevaporated to dryness
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d91b7ce263d141dcb1742818c3077b7b
Source dataset
uspto-grants-1998_12
Patent number
US05847127

Reaction notes

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