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

HRID 890201Notes

Reaction equation

HRID 890201 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-7a6a0f3546714918babc4a68edf0196e
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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