Reacción #58626

Ecuación de reacción

N-methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide

N-Methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide

methylmagnesium bromide

→

title compound

4-(4-Chlorophenyl)-3-phenyl-2-butanone

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction was quenched with methanol (5 mL) and 2 M hydrochloric acid (50 mL)
2. 2
   OtroThe volatile materials were removed
3. 3
   Concentraciónby concentrating on a rotary evaporator
4. 4
   Otrothe residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL)
5. 5
   OtroThe organic layer was separated
6. 6
   Extracciónthe aqueous layer was extracted with ether (2 times 200 mL) The combined organic extracts
7. 7
   Secadowere dried over anhydrous magnesium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated to dryness

Procedimiento

To a solution of N-methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide (Step C, 16 g, 53 mmol, dried by azeotroping with toluene) in anhydrous tetrahydrofuran (200 mL) at 0° C. was added methylmagnesium bromide (3 M in ether, 35 mL, 0.11 mol). After stirring at 0° C. for 2 h, the reaction was quenched with methanol (5 mL) and 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL). The organic layer was separated, and the aqueous layer was extracted with ether (2 times 200 mL) The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to dryness to give the title compound, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.45-7.02 (m, 9H), 4.08 (dd, 1H), 3.34 (dd, 1H), 2.90 (dd, 1H), 2.03 (s, 3H).

Fuente