(E)-1-(4-fluorophenyl)-2-Methylpent-1-en-3-one synthesis
- Product Name:(E)-1-(4-fluorophenyl)-2-Methylpent-1-en-3-one
- CAS Number:1170613-81-6
- Molecular formula:C12H13FO
- Molecular Weight:192.2294
Yield:1170613-81-6 76%
Reaction Conditions:
in tetrahydrofuran at -20 - 0; for 3 h;
Steps:
1.D (E)-1-(4-fluorophenyl)-2-methylpent-1-en-3-one
Example 1C
(7 g, 31.4 mmol) was dissolved in tetrahydrofuran (175 mL) and cooled to about -20° C. Ethylmagnesium bromide (1M in THF, 94 mL, 94 mmol) was added dropwise.
The solution was stirred while warming to about 0° C. for 3 hr.
The reaction was quenched with saturated NH4Cl solution, and then diluted with water.
The mixture was extracted with ethyl acetate.
The combined organic phase was washed with water and brine, dried over Na2SO4, filtered, and evaporated in vacuo.
The solid was chromatographed (SiO2, 10% ethyl acetate/hexanes) to afford the title compound as a yellow solid (4.59 g, 76% yield).
1H NMR (300 MHz, CDCl3) δ ppm 7.48 (s, 1H), 7.40 (dd, J=8.82, 5.43 Hz, 2H), 7.10 (t, J=8.65 Hz, 2H), 2.83 (q, J=7.12 Hz, 2H), 2.05 (d, J=1.36 Hz, 3H), 1.17 (t, J=7.29 Hz, 3H). MS (DCI+) 193 (M+H).
References:
US9108905,2015,B2 Location in patent:Page/Page column 23
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