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251310-52-8

ETHYL 2-[1-(4-NITROPHENYL)-4-PIPERIDINYLIDENE]ACETATE synthesis

5synthesis methods
-

Yield:251310-52-8 82%

Reaction Conditions:

in benzene; for 24 h;Product distribution / selectivity;Heating / reflux;

Steps:



Scheme 4a ; PPh3=CHCOOC2H5 Benzene; [00235] To anhydrous benzene (50 mL) was added 2 (1.32 g, 6 mmol) and Ph3P=CHCOOC2H5(4.18 g, 12 mmol). The reaction mixture was heated at reflux for 24 hours under an argon atmosphere. The reaction was cooled and the solvent removed under vacuum. The crude mixture was dissolved in ethyl acetate, concentrated, and chromatographed on silica gel using hexanes/ethyl acetate (8:3) to afford compound 3 (1.42g, 82%). The desired product is the first compound to be eluted from the column Rf ~ 0.7).1H NMR (400 MHz, CDCl3): δ 1.29 (t, 3H), 2.5 (d, 2H), 3.13 (t, 2H), 3.58 (m, 4H), 4.20 (q, 2H), 5.81 (s, IH), 6.79 (d, 2H), 8.13 (d, 2H). MALDI-TOF: 289, calcd 289.13.

References:

WO2008/130637,2008,A1 Location in patent:Page/Page column 32-33