Hydrochloric Acid → Phenyl(tetrahydro-2H-thiopyran-4-yl)methanone

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Diethyl Ether	HCID 3283	—
Reactant	Thiane-4-carbonitrile	HCID 21598641	—
Reactant	HCID 178418255	HCID 178418255	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Phenyl(tetrahydro-2H-thiopyran-4-yl)methanone	HCID 69290818	—

Reaction Steps

Tetrahydro-2H-thiopyran-4-carbonitrile (2.6 g, 20.5 mmol) and CuI (195 mg, 1 mmol) were diluted in dry THF (200 ml). A 1M solution of phenyl magnesium bromide in THF (41 ml, 41 mmol) was added and the mixture was heated at reflux for 16 hours. After cooling at room temperature, ether was added and the imine was hydrolyzed with a 1 N HCl solution for 10 minutes. The organic phase was separated and treated with a 0.1 N HCl solution for 10 minutes. The organic phase was separated and washed with brine, dried over MgSO4 and evaporated in vacuum. After chromatography on silica gel (CH2Cl2/hexane 30/70), the phenyl(tetrahydro-2H-thiopyran-4-yl)methanone 17 was obtained as a white solid (3 g, 70%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07361668B2
Source dataset	uspto-grants-2008_04
ORD ID	ord-dfd66986ba0d4db5a9580e8fab9bfee8
Source note	uspto-grants-2008_04