Reaktion #58626

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

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with methanol (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 times 200 mL) The combined organic extracts
7. 7
   Trocknenwere dried over anhydrous magnesium sulfate
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 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).

Quelle