반응 #58626

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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

용매

tetrahydrofuran

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후처리

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

실험 절차

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).

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