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

Participants

Role	Name	HCID	Charge
Reactant	3,5-Dichloro-2-pyridone	HCID 79496	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Reactant	3-(5-Chloro-2-pyridyloxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one	HCID 10157427	—
Solvent	Acetonitrile	HCID 6342	—
Product	3-(3,5-Dichloro-pyridin-2-yloxy)-4-(4-methanesulfonyl-phenyl)-5,5-dimethyl-5H-furan-2-one	HCID 21948521	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06020343
Source dataset	uspto-grants-2000_02
ORD ID	ord-0acadcb2bd7e4c3290ebdec917178573
Source note	uspto-grants-2000_02