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

HRID 890202Notes

Reaction equation

HRID 890202 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-1dc069704bc74b65afd80a761e85316b
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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