Triethylamine → Methyl 2-((trimethylsilyl)ethynyl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	Benzoic acid, 2-iodo-, methyl ester	HCID 69132	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Methyl 2-((trimethylsilyl)ethynyl)benzoate	HCID 11053512	85.1%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of 2-iodo-benzoic acid methyl ester (792 mg, 3.02 mmol) in DMF (10 mL) are added trimethylsilylacetylene (854 μL, 6.04 mmol) and triethylamine (2.95 mL, 21.1 mmol). The reaction mixture is degassed for 20 minutes with a stream of nitrogen. Dichloro(bistriphenylphosphene) palladium (II) (212 mg, 0.302 mmol, 10 mol %) and copper (I) iodide (58 mg, 0.302 mmol, 10 mol %) are added and the reaction is heated to 80° C. After 3 h, the reaction is concentrated and the residue is chromatographed eluting with 0 to 5% EtOAc/Hexanes to yield the title compound (597 mg, 85%). GC/MS: 232.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08106077B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-b3cb5dace8cb4b3cb449666ab2002aaa
Source note	uspto-grants-2012_01