Allyltributylstannane → 5-allyl-2-benzofuran-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-benzofuran-1(3H)-one (15.0 g, 70.4 mmol), allyl-tributyl-stannane (25.6 g, 77.5 mmol), LiCl (11.8 g, 282 mmol) and Pd(PPh3)4(1.2 g, 1 mmol) in 100 mL toluene was heated under N2 at 90-100° C. overnight. After cooling to r.t., the mixture was diluted with 250 mL EtOAc and filtered. The filtrate was washed with water and brine, dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified via silica column chromatography (DCM/Petrol Ether=1:5) to give 5-(prop-2-en-1-yl)-2-benzofuran-1(3H)-one.

Provenance & Evidence