Triphenylarsine → methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-vinylisobenzofuran-5-yl)-4-methyl-4-hexenoate

Participants

Role	Name	HCID	Charge
Reactant	Triphenylarsine	HCID 11773	—
Reactant	Tributylvinyltin	HCID 81998	—
Reactant	Lithium Chloride	HCID 433294	—
Reactant	Potassium Fluoride	HCID 522689	—
Reactant	methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-trifluoromethanesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate	HCID 10555649	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-vinylisobenzofuran-5-yl)-4-methyl-4-hexenoate	HCID 10672508	—

Reaction Conditions

Temperature	55 °C

Reaction Steps

A mixture of lithium chloride (4.8 g), tris(dibenzylideneacetone)-dipalladium (0) chloroform adduct (0.65 g), triphenylarsine (1.6 g) and methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-trifluoromethanesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoate (24.2 g) in N-methylpyrrolidinone (220 ml) was heated to 55° C. Vinyltributyltin (15 g) was added. After 3 hours the mixture was added to water (500 ml), potassium fluoride (16 g) and ethyl acetate. The organic solution was dried, filtered through celite and evaporated to afford methyl (E) 6-(1,3-dihydro-7-methyl-3-oxo-4-p-toluenesulfonyloxy-6-vinylisobenzofuran-5-yl)-4-methyl-4-hexenoate.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05525602
Source dataset	uspto-grants-1996_06
ORD ID	ord-afe32683f09a4b16b9eb05a066fd4271
Source note	uspto-grants-1996_06