Tetrahydrofuran → 1,4-Diethynylbenzene

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Triethylamine	HCID 8471	—
Reactant	p-Diiodobenzene	HCID 12208	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Dichloromethane	HCID 6344	—
Product	1,4-Diethynylbenzene	HCID 120463	—

Reaction Steps

Firstly, a mixture of 1,4-diiodobenzene (4 g, 12.1 mmol), PdCl2(PPh3)2 (340 mg, 0.484 mmol) and CuI (92.4 mg, 0.484 mmol), was added with dist. THF (20 mL), dist. Et3N (60 mL) and trimethylsilylacetylene (3.77 mL, 26.7 mmol). The resultant mixture was stirred under a nitrogen atmosphere at 80° C. for 22 hours to obtain a reaction mixture. Then, the reaction mixture was diluted with CH2Cl2. After that, an organic layer was washed with sat. NaCl, and dried with MgSO4. The dried organic layer was filtered and concentrated to obtain a crude product. The obtained crude product was separated and purified by silica gel column chromatography (hexane/EtOAc=10/1) to obtain 1,4-diethynylbenzene.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08053588B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-6034d2caa9fe431b851a0cf58f3e4f58
Source note	uspto-grants-2011_11