Tetrahydrofuran → 1-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Iodobenzene	HCID 11575	—
Reactant	Tetrabutylammonium Fluoride	HCID 2724141	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Triethylamine	HCID 8471	—
Product	1-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine	HCID 563609	90%

Reaction Steps

To a 4-mL vial, added 100 mg (0.28 mmol) (7) and 6 mg (0.0058 mmol) Pd2dba3-CHCl3. Next added 0.3 mL THF, 48 μL (0.43 mmol) iodobenzene, and finally 1.1 mL (1.1 mmol) TBAF solution (1M in THF). Let stir at room temperature for 18 hours. At the end of the reaction, added 200 μL triethylamine, let stir briefly, concentrated in vacuo, and purified the crude material directly by silica gel chromatography (automated column, 12 g SiO2, 0% to 20% EtOAc in hexanes gradient). Obtained 63 mg (90%) of 1-Benzyl-4-phenyl-1,2,3,6-tetrahydro-pyridine as a yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08013157B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-3202a8b2dbaf489a80ace91b344e8e53
Source note	uspto-grants-2011_09