3,5-Dichloro-2-pyridone → 3-(3,5-Dichloro-pyridin-2-yloxy)-4-(4-methanesulfonyl-phenyl)-5,5-dimethyl-5H-furan-2-one

HRID 565108Notes

Reaction equation

HRID 565108 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[C:10](=[O:26])[O:11][C:12]([CH3:25])([CH3:24])[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[N:6][CH:7]=1.[Cl:27]C1C(=O)NC=C(Cl)C=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH3:25][C:12]1([CH3:24])[O:11][C:10](=[O:26])[C:9]([O:8][C:5]2[C:4]([Cl:27])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[C:13]1[C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 794963,5-Dichloro-2-pyridoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 101574273-(5-Chloro-2-pyridyloxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

Product 1

HCID 219485213-(3,5-Dichloro-pyridin-2-yloxy)-4-(4-methanesulfonyl-phenyl)-5,5-dimethyl-5H-furan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a R.T. solution of 2-chloroacetic acid 2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one ester (954 mg, 3 mmol, example 25) in acetonitrile (15 mL) was added 3,5-dichloro-2-pyridone (656 mg, 4.0 mmol) followed by DBU (2.28 g, 15 mmol) and the mixture was slowly warmed up to gentle reflux for 2 hours. The mixture was cooled to 25° C. the volatiles were removed in vacuo. The residue was purified on silica gel chromatography (1/1, EtOAc/Hexanes then 100% EtOAc)) to provide the title compound.

Workup

  1. temperaturethe mixture was slowly warmed up
  2. temperatureto gentle reflux for 2 hours
  3. customwere removed in vacuo
  4. customThe residue was purified on silica gel chromatography (1/1, EtOAc/Hexanes

Sources & evidence

ORD record
ord-92cacdd0c8374ba78ed192953b750930
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Reaction notes

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