Cyclopropyl(4-pyridyl) ketone synthesis
- Product Name:Cyclopropyl(4-pyridyl) ketone
- CAS Number:39512-48-6
- Molecular formula:C9H9NO
- Molecular Weight:147.17
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Yield:-
Reaction Conditions:
Stage #1: pyridine-4-carbonitrile;cyclopropylmagnesium bromide in tetrahydrofuran at 0 - 20;
Stage #2: with hydrogenchloride;water in tetrahydrofuran;
Steps:
1
Step 1: Cyclopropyl(pyridin-4-yl)methanoneCyclopropylmagnesium bromide (7.5 g, 62.28 mmol) in dry THF (40 ml) was added dropwise to a solution of 4-cyanopyridine (2.16 g, 20.7 mmol) in dry THF (50 ml) at 0 °C. The reaction mixture was left to warm slowly to room temperature. After 5 hours stirring at room temperature, the reaction was quenched with 1M HC1. The reaction mixture was then alkalified using aq. NaOH (10%), extracted with dichloromethane, dried (Na2S04) and concentrated under reduce pressure. The residue was purified by column chromatography. 2.46 g of the title compound was obtained.1H NMR (400 MHz, CDC13) 5 ppm 1.18-1.12 (m, 2H), 1.31-1.28 (m, 2H), 2.67-2.62 (m, 1H), 7.79-7.77 (m, 2H), 8.82-8.80 (m, 2H).
References:
WO2012/152983,2012,A1 Location in patent:Page/Page column 45
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