Reacción #53305

Ecuación de reacción

potassium phthalimide

2,6-Dimethylbenzyl Alcohol

chlorotrimethylsilane

→

title compound

N-(2,6-Dimethylbenzyl)phthalimide

Disolventes

ethyl acetate

water

ethyl acetate

DMF

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe organic layer was washed with brine
2. 2
   Secadodried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   Otroto give an oil
6. 6
   workup.STIRRINGThe reaction mixture was stirred for 16 hours at room temperature
7. 7
   Lavadothe organic layer was washed with 3% Na2CO3, 1 N HCl
8. 8
   Secadodried over Na2SO4
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated
11. 11
    Otroto give white solid
12. 12
    OtroThe purification

Procedimiento

To a stirred solution of 2,6-Dimethylbenzyl Alcohol (Step A, 6.59 g, 48.4 mmol) in DMSO (20 ml) was added chlorotrimethylsilane (15.75 ml, 145 mmol) at room temperature, and the mixture was stirred for one hr. To this reaction mixture were added ethyl acetate and water, the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give an oil. The oily residue was redissolved in DMF (100 ml) and potassium phthalimide (10.76 g, 58.1 mmol) was added. The reaction mixture was stirred for 16 hours at room temperature, ethyl acetate was added, and the organic layer was washed with 3% Na2CO3, 1 N HCl, dried over Na2SO4, filtered and concentrated to give white solid. The purification was done by flash chromatography on silica gel column (chloroform:methanol 95:5) to provide the title compound as white solid.

Fuente