2-Acetylbutyrolactone → HCID 178424661, compound

HRID 966008Notes

Reaction equation

HRID 966008 reaction equation
[C:1]1([CH3:18])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[NH:13][C:12]([CH3:14])=[N:11][C:10]=1[N+:15]([O-])=O.[C:19]([CH:22]1[CH2:27][CH2:26][O:25][C:23]1=[O:24])(=O)[CH3:20]>C(O)C.C(O)(=O)C.[Fe]>[OH:25][CH2:26][CH2:27][C:22]1[C:19]([CH3:20])=[N:15][C:10]2[N:11]([C:12]([CH3:14])=[N:13][C:9]=2[C:2]2[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=2[CH3:18])[C:23]=1[OH:24]

Participants

6

Reactant 2

HCID 106012-AcetylbutyrolactoneHCID 178424685HCID 178424685, compound

Product 1

HCID 178424661HCID 178424661, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 5-mesityl-2-methyl-4-nitro-1H-imidazole (2.1 g, 8.56 mmol), α-acetyl-γ-butyrolactone (1.21 g, 9.42 mmol), and iron powder (2.39 g, 42.8 mmol) in ethanol (40 mL) and acetic acid (10 mL) was stirred at 80° C. for one day. The mixture was filtered through Celite and evaporated. The resulting crystals were washed with ethyl acetate, to give the title compound (0.95 g) as white crystals.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated
  3. washThe resulting crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-a5535697ba7b4272bd0ee0945df8e4ba
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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