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ChemicalBook CAS DataBase List 1-Ethoxy-3-trifluoromethyl-1,3-butadiene

1-Ethoxy-3-trifluoromethyl-1,3-butadiene synthesis

6synthesis methods
-

Yield:59938-06-6 87%

Reaction Conditions:

with dmap;trifluoroacetic anhydride in 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

Steps:

14.A Preparation of Substituted Quinolines 88
Step A: Preparation of 4-ethoxy-trifluoro-but-3-en-2-one 84. Ethylvinylether (5 g, 1 eq.) was added dropwise at -10° C. and under nitrogen to a stirred solution of trifluoroacetic anhydride (10 mL, 1.05 eq.) and 4-dimethylaminopyridine (80 mg, 0.06 eq.) in DCM (90 mL). The reaction mixture was stirred at 0° C. for 8 hrs and allowed to warm up at room temperature overnight. The mixture was then poured into cold aqueous NaHCO3 solution. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 84 as brown oil in 87% yield. 1H NMR (CDCl3, 400 MHz) δ 1.39-1.43 (t, J=7.04 Hz, 3H), 4.08-4.13 (q, J=7.04 Hz, 2H), 5.86 (d, J=12.40 Hz, 1H), 7.90 (d, J=12.40 Hz, 1H).

References:

Idenix Pharmaceuticals, Inc. US2009/202480, 2009, A1

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