2-Acetylbutyrolactone → 3-1-[(4-Mesityl-3-pyridyl)amino]ethylidenetetrahydro-2-furanone

HRID 966019Notes

Reaction equation

HRID 966019 reaction equation
[C:1]1([CH3:16])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH2:15].[C:17]([CH:20]1[CH2:25][CH2:24][O:23][C:21]1=[O:22])(=O)[CH3:18]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]1([CH3:16])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH:15][C:17](=[C:20]1[CH2:25][CH2:24][O:23][C:21]1=[O:22])[CH3:18]

Participants

5

Reactant 2

HCID 106012-AcetylbutyrolactoneHCID 222494794-Mesityl-3-pyridinamine

Product 1

HCID 695835403-1-[(4-Mesityl-3-pyridyl)amino]ethylidenetetrahydro-2-furanoneYield 77.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.2 g, 1.18 mmol) was added to a solution of 4-mesityl-3-pyridinamine (5.0 g, 24 mmol) and α-acetyl-γ-butyrolactone (6.0 g, 47 mmol) in toluene (100 mL), followed by heating under reflux for three days while removing water using a Dean-Stark apparatus. The mixture was evaporated, and the resulting crystals were washed with 60% diethyl ether/ethyl acetate, to give the title compound (6.0 g) as white crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for three days
  3. customwhile removing water using a Dean-Stark apparatus
  4. customThe mixture was evaporated
  5. washthe resulting crystals were washed with 60% diethyl ether/ethyl acetate

Sources & evidence

ORD record
ord-746587b49d0e4aa4ab39581de335cb1c
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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