3-Methyl-1(3H)-isobenzofuranone → (3E)-3-(3-methyl-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Temperature

0 °C

To a solution of oxindole (119 mg, 0.891 mmol) in THF (2.0 ml) cooled at 0° C. was added 1.0M LiHMDS/THF (1.78 ml). The mixture was stirred for 4 minutes at 0° C., then allowed to warm to room temperature for an additional 6 minutes. A solution of 3-methyl-2-benzofuran-1(3 H)-one (119 mg, 0.802 mmol) in THF (0.5 ml) was added, and the reaction was rapidly stirred for 1.5 hours. The reaction was quenched into 10% HCl aqueous solution (30 ml). The resulting mixture was stirred 5 minutes, and then extracted into EtOAc. The combined organic layers were washed with water, brine, dried with anhydrous Na2SO4, and rotary evaporated to a yellow oil. Upon standing at room temperature overnight a yellow crystalline solid formed from the yellow oil. The remaining oil was removed by pipet and the solid was recrystallized from EtOAc to produce (3E)-3-(3-methyl-2-benzofuran-1(3 H)-ylidene)-1,3-dihydro-2H-indol-2-one as a yellow solid (32 mg, 15%).

1. temperatureto warm to room temperature for an additional 6 minutes
2. stirringthe reaction was rapidly stirred for 1.5 hours
3. customThe reaction was quenched into 10% HCl aqueous solution (30 ml)
4. stirringThe resulting mixture was stirred 5 minutes
5. extractionextracted into EtOAc
6. washThe combined organic layers were washed with water, brine
7. dry with materialdried with anhydrous Na2SO4
8. customrotary evaporated to a yellow oil
9. waitUpon standing at room temperature overnight
10. customa yellow crystalline solid formed from the yellow oil
11. customThe remaining oil was removed by pipet
12. customthe solid was recrystallized from EtOAc

ORD record

ord-72f8093c86394adbba71d874bccdf1b6

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060844B2