Trimethylsilylacetylene → [4-(1-Methoxycyclopropyl)phenylethynyl]-trimethylsilane

Participants

Role	Name	HCID	Charge
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	HCID 22568990	HCID 22568990	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Triethylamine	HCID 8471	—
Product	[4-(1-Methoxycyclopropyl)phenylethynyl]-trimethylsilane	HCID 22568890	90%

Reaction Conditions

Temperature	70 °C

Reaction Steps

Using General Procedure D; 1-bromo-4-(1-methoxycyclopropyl)-benzene (Intermediate 59, 300.0 mg, 1.32 mmol) in triethylamine (4 mL) and anhydrous tetrahydrofuran (4 mL) was treated with copper(I)iodide (93.0 mg, 0.13 mmol) and then sparged with argon for 5 minutes. Trimethylsilyl acetylene (1.39 g, 14.2 mmols) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (93.0 mg, 0.13 mmol). The resulting reaction mixture was heated to 70° C. for 60 h. The title compound (286.0 mg, 90%) was isolated by chromatography (0-3% EtOAc—hexanes).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06855512B2
Source dataset	uspto-grants-2005_02
ORD ID	ord-e289f74fe4c147b5a0c747d7f322ff2f
Source note	uspto-grants-2005_02