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

HRID 966024

Reaction equation

HRID 966024 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-5a95d79f963c47cfb60e1135f1379845
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Linked notes

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