Sodium Carbonate → ethyl 5-phenyl-3,6-dihydro-2H-pyran-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate	HCID 86638856	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	ethyl 5-phenyl-3,6-dihydro-2H-pyran-4-carboxylate	HCID 67311476	78%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate (1.77 g, 5.81 mmol) and phenylboronic acid (1.42 g, 11.62 mmol) in dioxane (15 ml) was added Pd(dppf)Cl2 (430 mg, 0.58 mmol) and Na2CO3 (1.85 g, 17.46 mmol) in water (4.5 mL), the mixture was degassed with N2 for 5 min, and was heated at 100° C. for 15 h, after cooling to room temperature the mixture was diluted with EtOAc and washed with Sat. NaHCO3 and brine, organic layer was combined, dried and concentrated to give crude product, which was purified by column chromatography (Hexanes/EtOAc=4:1) to give ethyl 5-phenyl-3,6-dihydro-2H-pyran-4-carboxylate (1.05 g, 78%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09422279B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-81d2d1f68d254fb58d08886626f2c951
Source note	uspto-grants-2016_08