2-(2-OXO-2-PHENYL-ETHYL)-CYCLOHEXANONE synthesis
- Product Name:2-(2-OXO-2-PHENYL-ETHYL)-CYCLOHEXANONE
- CAS Number:33553-23-0
- Molecular formula:C14H16O2
- Molecular Weight:216.28
Yield:33553-23-0 91%
Reaction Conditions:
Stage #1: 1-(1-Cyclohexen-1-yl)pyrrolidine;α-bromoacetophenonewith sodium iodide in 1-methyl-pyrrolidin-2-one at 20; for 11 h;
Stage #2: with water in 1-methyl-pyrrolidin-2-one; for 11 h;Product distribution / selectivity;
Steps:
3.2
To a 250-mL round-bottomed flask containing 2.4 mL of 1-cyclohex-l-en-l-ylpyrrolidine was added 20 mL anhydrous NMP followed by NaI (0.645 g), under nitrogen. The flask was fitted with an addition funnel containing 2-bromo-l-phenylethanone (4.12 g) dissolved in 35 mL anhydrous NMP, which was dropped into the enamine solution over 60 min. This solution was stirred at ambient temperature for 1Oh, then 90 mL of water was added to the solution and it was stirred for another 11 hours, under nitrogen. The solution was then extracted twice with ethyl acetate and water, the organic layers combined and further washed with water (3x), dried over sodium sulphate, filtered and evaporated to give a yellow oil. The oil was purified by Flash chromatography using a gradient cyclohexane: EtOAc (9:1). The product 2-(2-oxo-2-phenylethyl)cyclohexanone was used directly for the next reaction. (4.1 g, 91% yield, 98% purity by HPLC). MS(ESI+): 217.4; MS(ESI ): 215.6.
References:
WO2008/116926,2008,A1 Location in patent:Page/Page column 48; 49
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