Reaktion #220615

Reaktionsgleichung

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with MeOH (5 mL) and 2 M hydrochloric acid (50 mL)
2. 2
   SonstigeThe volatile materials were removed
3. 3
   Einengenby concentrating on a rotary evaporator
4. 4
   Sonstigethe residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL)
5. 5
   SonstigeThe organic layer was separated
6. 6
   Extraktionthe aqueous layer was extracted with ether (2×200 mL)
7. 7
   TrocknenThe combined organic extracts were dried over anhydrous MgSO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated to dryness

Vorschrift

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 THF (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 MeOH (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 (2×200 mL). The combined organic extracts were dried over anhydrous MgSO4, 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).

Quelle