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

HRID 584815

Reaction equation

HRID 584815 reaction equation
[C:1]1([CH3:17])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[C:10]([CH3:16])=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].[C:18]([CH:21]1[CH2:26][CH2:25][O:24][C:22]1=[O:23])(=O)[CH3:19]>C(O)C>[C:1]1([CH3:17])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[C:10]([CH3:16])=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH:12][C:18](=[C:21]1[CH2:26][CH2:25][O:24][C:22]1=[O:23])[CH3:19]

Participants

4

Reactant 2

HCID 106012-AcetylbutyrolactoneHCID 222495383-Mesityl-2-methylaniline

Product 1

HCID 695835283-[1-(3-Mesityl-2-methylanilino)ethylidene]tetrahydro-2-furanoneYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-mesityl-2-methylaniline (5.0 g, 22 mmol) and α-acetyl-γ-butyrolactone (14.2 g, 0.11 mol) in ethanol (100 mL) was heated at reflux for three days. The mixture was evaporated, and the residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (7.08 g) as white crystals.

Workup

  1. temperatureat reflux for three 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-aa75fcc7501d4cd68fb8d5995ad2fc31
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Linked notes

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