Triethylamine → (4,4-Dibutylthiochroman-6-yl)(trimethylsilyl)acetylene

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	6-Bromo-4,4-dibutylthiochroman	HCID 18322011	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Dichlorobis(triphenylphosphine)palladium	HCID 6102075	—
Product	(4,4-Dibutylthiochroman-6-yl)(trimethylsilyl)acetylene	HCID 18321992	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

A mixture of 1.68 g (5.38 mmol) of 6-bromo-4,4-dibutylthiochroman (Compound 33), 0.28 g (1.5 mmol) of copper (I) iodide and 2.5 g (25 mmol) of triethylamine was degassed with argon for 15 minutes at -78° C. To the suspension was added 1.18 g (71 mmol) of (trimethylsilyl)acetylene and 0.24 g (0.3 mmol) of bis(triphenylphosphine)palladium (II) chloride. The solution was degassed with argon for an additional 5 minutes and the resulting mixture was allowed to warm to 0° C. The tube was sealed and the mixture was heated to 55° C. for 22 hours.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05663347
Source dataset	uspto-grants-1997_09
ORD ID	ord-6daf9e1b91d649f9b478f6227dd49b35
Source note	uspto-grants-1997_09