Ethyl Acetate → p-methylcarbonylstyrene

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	1-(4-Iodophenyl)ethan-1-one	HCID 72869	—
Reactant	Tributylvinyltin	HCID 81998	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Tris(furan-2-yl)phosphane	HCID 521585	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Dimethylformamide	HCID 6228	—
Product	p-methylcarbonylstyrene	HCID 10909702	101.8%

Reaction Steps

To a stirred mixture of 4-iodoacetophenone (1.0 g, 4.1 mmol), Pd2(dba)3 (186 mg, 0.2 mmol), P(2-furyl)3 (94 mg, 0.4 mmol), and CuI (77 mg, 0.4 mmol) in 20 mL of anhydrous DMF under N2 atmosphere was added vinyltributyltin (1.43 mL, 4.9 mmol) via syringe. An exothermic reaction was observed. After stirred for over night at r.t., the reaction mixture was poured into EtOAc (20 mL), washed with sat. aq. CsF solution, and brine. The organic layer was dried over Na2SO4, evaporated. The titled compound (610 mg, 100%) was isolated after silica gel MPLC eluting with 0–15% EtOAC in hexanes.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07119205B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-3819e07442814a6c8428cf236febba4e
Source note	uspto-grants-2006_10