Butyl vinyl ether → 5-(1-butoxy-vinyl)-4-methyl-3H-isobenzofuran-1-one

Participants

Reaction Conditions

Reaction Steps

To a 1 L 3-neck was charged trifluoromethanesulfonic acid, 4-methyl-1-oxo-1,3-dihydro-isobenzofuran-5-yl ester (63.0 g, 213 mmol), DMF (315 mL), butyl vinyl ether (138 mL, 1063 mmol)), and then Et3N (35.6 mL, 255 mmol). The solution was sparged with N2 for 20 minutes. To the solution was added Pd(OAc)2 (1.19 g, 5.32 mmol) and DPPP (2.41 g, 5.85 mmol), and the solution was then sparged for an additional 10 minutes, and then heated to 80° C. After a 1 hour age, the solution was cooled to <10° C., quenched with 630 mL EtOAc, and then washed with 5% NH4Cl (2×315 mL) and 10% brine (2×315 mL). The solution was then dried over MgSO4, filtered, concentrated by rotary evaporation and flushed with EtOAc (3×100 mL) to remove excess butyl vinyl ether, providing crude 5-(1-butoxy-vinyl)-4-methyl-3H-isobenzofuran-1-one.

Provenance & Evidence