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

HRID 890193Notes

Reaction equation

HRID 890193 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[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=1.[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[C:14]([NH:15][C:17](=[C:20]2[CH2:25][CH2:24][O:23][C:21]2=[O:22])[CH3:18])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 106012-AcetylbutyrolactoneHCID 167414262-Mesityl-3-pyridinamine

Product 1

HCID 695835203-1-[(2-Mesityl-3-pyridyl)amino]ethylidenetetrahydro-2-furanoneYield 64.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

p-Toluenesulfonic acid monohydrate (39 mg, 0.20 mmol) was added to a solution of 2-mesityl-3-pyridinamine (3.9 g, 18 mmol) and α-acetyl-γ-butyrolactone (4.7 g, 37 mmol) in toluene (80 mL). The mixture was heated under reflux for seven days while removing water using Dean-Stark apparatus. The mixture was evaporated, and the resulting crystals were washed with 60% diethyl ether/ethyl acetate, to give the title compound (3.74 g) as white crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for seven days
  3. customwhile removing water using 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-0b8b5f96ce2a4e83a4cedaf33e6e73c3
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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