Trimethylsilylacetylene → Ethyl 5-(2-trimethylsilyl-ethyn-1-yl)-thiophene-2-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	Ethyl 5-bromothiophene-2-carboxylate	HCID 605723	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Diisopropylamine	HCID 7912	—
Product	Ethyl 5-(2-trimethylsilyl-ethyn-1-yl)-thiophene-2-carboxylate	HCID 66974178	98.4%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of ethyl 5-bromo-thiophene-2-carboxylate (500 mg, 2.13 mmol), trimethylsilylacetylene (0.445 mL, 3.2 mmol), Pd(PPh3)4 (15 mg) and CuI (10 mg) in diisopropylamine (10 mL) was heated at 80° C. for 2 h. After being cooled to room temperature, the mixture was filtered through CELITE, and the filtrate was poured into water. The product was extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, concentrated in vacuo to give ethyl 5-(2-trimethylsilyl-ethyn-1-yl)-thiophene-2-carboxylate (529 mg). MS 253 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08349873B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-648e13c425274737aa7ed4313c18f7e4
Source note	uspto-grants-2013_01