Ammonium Chloride → Ethyl 4-(3,3,3-trifluoro-propylidene)-cyclohexanecarboxylate

n-Butyllithium (1.6 M solution in hexane, 26 ml, 41.6 mmol) was added to a solution of triphenyl-(3,3,3-trifluoro-propyl)-phosphonium iodide (20.25 g, 41.64 mmol) in THF (141 ml) at −78° C. over 13 minutes, and the mixture was stirred at the same temperature for 20 minutes. A solution of 4-oxo-cyclohexanecarboxylic acid ethyl ester (6.56 g, 38.54 mmol) in THF (22 ml) was added to the reaction solution at −78° C. over 17 minutes, and the mixture was stirred at the same temperature for one hour. A 50% saturated aqueous ammonium chloride solution was added, followed by extraction with dichloromethane. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give ethyl 4-(3,3,3-trifluoro-propylidene)-cyclohexanecarboxylate (9.25 g, 96%).

1. stirringthe mixture was stirred at the same temperature for one hour
2. extractionfollowed by extraction with dichloromethane
3. dry with materialThe organic layer was then dried over MgSO4
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

ORD-Eintrag

ord-41355dc934384b049f88857382137aa4

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09169254B2