Reacción #58663

Ecuación de reacción

4-chlorobenzyl bromide

2-(1H-1,2,3-benzotriazol-1-yl)-N-methoxy-N-methylacetamide

lithium bis(trimethylsilyl)amide

→

desired product

2-(1H-1,2,3-Benzotriazol-1-yl)-3-(4-chlorophenyl)-N-methoxy-N-methyl-propanamide

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   workup.STIRRINGstirred for 6 h
3. 3
   OtroThis reaction was quenched
4. 4
   workup.ADDITIONdiluted with 75 mL EtOAc
5. 5
   Lavadowashed 3 times with 10 mL each of brine
6. 6
   OtroAfter drying
7. 7
   Otrothe organic phase solvent removal
8. 8
   Otroafforded a crude product which
9. 9
   Otrowas purified on silica gel using 40% EtOAc in hexane as solvent

Procedimiento

To a solution of 2.0 g (9 mmol) of 2-(1H-1,2,3-benzotriazol-1-yl)-N-methoxy-N-methylacetamide in 15 mL anhydrous THF at −78° C., 10 mL (10 mmol) of 1M lithium bis(trimethylsilyl)amide was added dropwise. After stirring for 25 min, a solution of 2.06 g (10 mmol) of 4-chlorobenzyl bromide in 2 mL anhydrous THF was added. The resulting reaction mixture was allowed to warm to RT and stirred for 6 h. This reaction was quenched, diluted with 75 mL EtOAc and washed 3 times with 10 mL each of brine, After drying the organic phase solvent removal afforded a crude product which was purified on silica gel using 40% EtOAc in hexane as solvent to afford the desired product as a solid. 1H NMR: (CDCl3): δ 3.2 (s, 3H), 3.34 (s, 3H), 3.52 (m, 1H), 3.7 (m, 1H), 6.32 (t, 1H), 6.9-8.2 (m, 8H).

Fuente