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CHEMBRDG-BB 3018393 synthesis

5synthesis methods
-

Yield:58621-54-8 100%

Reaction Conditions:

with potassium carbonate in acetone at 20;Reflux;

Steps:

154.154-a-1

Example 154; Preparation of 3-((4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy)pyridin-2-yl)methyl)-5-methyl-5-(2-methyl-2,3-dihydrobenzofuran-6-yl)imidazolidine-2,4-dione; 154-a-1) Preparation of 1-(3-(allyloxy)phenyl)ethanone; 3-Hydroxyacetophenone (1.36 g, 10.0 mmol) was dissolved in acetone (50 mL), then added with potassium carbonate (2.76 g, 20.0 mmol) and allylbromide (1.27 mL, 15.0 mmol) at room temperature, and heated to reflux for 2 hours. The reaction solution was cooled to room temperature, added with ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (n-hexane/ethyl acetate=10/1), and 1-(3-(allyloxy)phenyl)ethanone (1.76 g, 100%) was obtained as a pale yellow oil.1H-NMR (CDCl3) δ: 2.59 (3H, s), 4.60 (2H, d, J=5.4 Hz), 5.31 (1H, dd, J=1.5, 10.5 Hz), 5.43 (1H, dd, J=1.5, 17.3 Hz), 6.02-6.11 (1H, m), 7.13 (1H, d, J=8.3 Hz), 7.37 (1H, t, J=7.8 Hz), 7.50-7.55 (1H, m).

References:

US2010/48610,2010,A1 Location in patent:Page/Page column 86