2-Acetylbutyrolactone → 3-[1-(3-Iodoanilino)ethylidene]tetrahydro-2-furanone

HRID 584816

Reaction equation

HRID 584816 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([CH:12]1[CH2:17][CH2:16][O:15][C:13]1=[O:14])(=O)[CH3:10]>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH:5][C:9](=[C:12]1[CH2:17][CH2:16][O:15][C:13]1=[O:14])[CH3:10]

Participants

4

Reactant 2

HCID 106012-AcetylbutyrolactoneHCID 122713-Iodoaniline

Product 1

HCID 695835373-[1-(3-Iodoanilino)ethylidene]tetrahydro-2-furanoneYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-iodoaniline (5.0 g, 23 mmol), α-acetyl-γ-butyrolactone (14.6 g, 0.11 mol) in ethanol (100 mL) was heated under reflux for seven days. The mixture was evaporated, and the residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (7.54 g) as white crystals.

Workup

  1. temperatureunder reflux for seven days
  2. customThe mixture was evaporated
  3. customthe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7804268827954dbcae14ead23b34b792
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Linked notes

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