Triphenylphosphine → 2-(4-Phenylbut-1-ynyl)benzo[d]oxazole

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	2-Chlorobenzoxazole	HCID 11986	—
Reactant	4-Phenyl-1-butyne	HCID 123360	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Triethylamine	HCID 8471	—
Product	2-(4-Phenylbut-1-ynyl)benzo[d]oxazole	HCID 11565027	40.5%

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of CuI (15 mg, 81 mmol) in triethylamine (3 mL) were added 2-chlorobenzo[d]oxazole (250 mg, 1.63 mmol), (PPh3)2PdCl2 (57 mg, 81 μmol), triphenylphosphine polymer bound 3 mmol/g (98 mg, 293 μmol) and a solution of 1-(but-3-ynyl)benzene (250 mg, 1.92 mmol) in DMF (0.5 mL). The reaction mixture was stirred for 25 min. at 120° C. in the microwave cavity. The reaction was quenched as described in Example 1. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 95:5) to yield 163 mg (0.66 mmol, 40%) of 2-(4-phenylbut-1-ynyl)benzo[d]oxazole as an orange oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883826B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-0cda3b02d8404878ba77c92541c44658
Source note	uspto-grants-2014_11