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

HRID 966023

Reaction equation

HRID 966023 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-11005c9704b04b879c82343c94928319
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Linked notes

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