2-Acetylbutyrolactone → HCID 178424661, compound

HRID 890186Notes

Reaction equation

HRID 890186 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-482812a53a764981b6e5e678eb1d09d7
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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