3,3-Dimethylphthalide → HCID 58649234, compound

Temperature

0 °C

To a solution of oxindole (127 mg, 0.956 mmol) in THF (2.0 ml) cooled at 0° C. was added 1.0M LiHMDS in THF (1.91 ml). The mixture was stirred for 4 minutes at 0° C., then allowed to warm to room temperature for an additional 6 minutes. The solid 3,3-dimethyl-2-benzofuran-1(3H)-one (140 mg, 0.86 mmol) was added in one portion and the reaction rapidly stirred for 1.5 hours. The reaction was quenched into 30 ml 10% HCl aqueous solution. 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. The yellow oil was chromatographed through silica gel column (20% to 30% EtOAc/hexane gradient) to give (3E)-3-(3,3-dimethyl-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one as a yellow solid (99 mg, 41%).

1. temperatureto warm to room temperature for an additional 6 minutes
2. customthe reaction
3. stirringrapidly stirred for 1.5 hours
4. customThe reaction was quenched into 30 ml 10% HCl aqueous solution
5. stirringThe resulting mixture was stirred 5 minutes
6. extractionextracted into EtOAc
7. washThe combined organic layers were washed with water, brine
8. dry with materialdried with anhydrous Na2SO4
9. customrotary evaporated to a yellow oil
10. customThe yellow oil was chromatographed through silica gel column (20% to 30% EtOAc/hexane gradient)

ORD record

ord-3900dfe860f644679e5b725ecbce0fe8

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060844B2