Tetrahydrofuran → HCID 59806151, compound

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	Bis(4-iodophenyl)acetylene	HCID 11048257	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 59806151	HCID 59806151	—

Reaction Steps

Firstly, a mixture of 4,4′-diiodotolan (171 mg, 0.40 mmol), PdCl2(PPh3)2 (27.9 mg, 0.040 mmol) and CuI (7.6 mg, 0.040 mmol) was added with dist. THF (3 mL), dist. Et3N (3 mL) and trimethylsilylacetylene (140 μL, 0.99 mmol). The resultant mixture was then stirred under a nitrogen atmosphere at 50° C. for 17 hours to obtain a reaction mixture. Subsequently, the reaction mixture was diluted with CH2Cl2. After that, an organic layer was washed with sat. NaCl, and the washed organic layer was then dried with MgSO4. The dried organic layer was filtered and concentrated to obtain a crude product (I). The obtained crude product (I) was separated and purified by silica gel column chromatography (hexane/EtOAc=10/1) to obtain 4,4′-bis(trimethylsilylethynyl)tolan.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08053588B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-315e6b72c12c4ae9b03e85e5115c85fc
Source note	uspto-grants-2011_11