Réaction #214158

Équation de réaction

2-(4-chlorophenyl)-3-methylbutyramide

3-phenoxybenzyl bromide

dichloromethane

→

3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanimidate

Solvants

ether

ethyl ether

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture is refluxed for 2 hours
2. 2
   Autreseparated
3. 3
   workup.ADDITIONby pouring into ice cold aqueous ethyl acetate/sodium bicarbonate
4. 4
   LavageThe organic phase is washed with water
5. 5
   Autredried
6. 6
   AutreThe residue is triturated with ether
7. 7
   Filtrationfiltered
8. 8
   ConcentrationThe filtrate is concentrated
9. 9
   Autrechromatographed on silica gel
10. 10
    Lavageeluting with 25% ethyl acetate/hexane

Mode opératoire

To a refluxing solution of 2.72 g (12.9 mmol) of 2-(4-chlorophenyl)-3-methylbutyramide and 2.27 g (8.6 mmol) of 3-phenoxybenzyl bromide in a solution of 15 ml dichloromethane and 3 ml ethyl ether is added a solution of 1.83 g (9.5 mmol) of silver tetrafluoroborate in ether. The mixture is refluxed for 2 hours and then separated by pouring into ice cold aqueous ethyl acetate/sodium bicarbonate. The organic phase is washed with water, dried and stripped of solvent. The residue is triturated with ether and filtered. The filtrate is concentrated and chromatographed on silica gel, eluting with 25% ethyl acetate/hexane, and then on plates using 35% ethyl acetate/hexane, to yield 3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanimidate, MS m/e 393 (M+).

Source