Sodium Iodide → 2-((3,3-Dimethyl)oxindolyl)ethanol

Temperature

75 °C

3,3-Dimethylindol-1,3-dihydro-2H-indol-2-one (6.3 g, 40 mmol) was dissolved in dry dimethylformamide under nitrogen at room temperature. Sodium hydride (60% dispersion in mineral oil, 1.8 g, 45 mmol) was added and the mixture was stirred until gas evolution ceased. 2-(2-Chloroethoxy)tetrahydro-2H-pyran (7.5 g, 42 mmol) and sodium iodide (0.6 g, 4 mmol) was added and the mixture was warmed to 75° C. for 15 hours. Water was added and the mixture was concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed (×3) with water, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting oil was taken up in methanol, para toluenesulphonic acid (0.75 g, 4 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was concentrated under reduced pressure, taken up in ethyl acetate, washed (×3) with aqueous sodium hydrogen carbonate solution dried (MgSO4), filtered and concentrated under reduced pressure. The resulting oil was purified by chromatography on silica gel, eluent hexane/ethyl acetate, to give 3,3-dimethyl-1-(2-hydroxy-1-ethyl)indol-2(3H)-one which was characterised by 1H nmr and MS.

1. concentrationthe mixture was concentrated under reduced pressure
2. washwashed (×3) with water
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. stirringthe mixture was stirred at room temperature for 12 hours
7. concentrationThe mixture was concentrated under reduced pressure
8. washwashed (×3) with aqueous sodium hydrogen carbonate solution
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe resulting oil was purified by chromatography on silica gel, eluent hexane/ethyl acetate

ORD record

ord-5c643ba2926f40b0ade02889d1c902d0

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05773448