2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide → HCID 178447863, compound

Temperature

-30 °C

A mixture of 531 g (1170 mmol) of 2-(1,3-dioxane-2-yl)ethyltriphenylphosphonium bromide and 4.0 l of THF was cooled to −30° C. under a nitrogen gas stream with a refrigeration medium. To this mixture, 121 g (1080 mmol) of t-BuOK was added, followed by stirring for 1 hour. Furthermore, 1 l of a THF solution containing 200 g (899 mmol) of 4-(trans-4-propylcyclohexyl)cyclohexanone was added dropwise to the mixture, while the temperature was maintained at −30° C. or less. After the dropping, the reaction temperature was slowly raised to room temperature, and the solution was further stirred for 5 hours. Next, the reaction solution was filtered through Celite, and the solvent was then distilled off under reduced pressure. The resulting residue was purified through silica gel column chromatography (a developing solvent: a mixed solvent of toluene/ethyl acetate=9/1 (v/v)) to obtain 277 g of crude 2-(2-(4-(trans-4-propylcyclohexyl)cyclohexylidene)ethyl)-1,3-dioxane.

1. additionwas added dropwise to the mixture, while the temperature
2. temperaturewas maintained at −30° C. or less
3. temperatureAfter the dropping, the reaction temperature was slowly raised to room temperature
4. stirringthe solution was further stirred for 5 hours
5. filtrationNext, the reaction solution was filtered through Celite
6. distillationthe solvent was then distilled off under reduced pressure
7. customThe resulting residue was purified through silica gel column chromatography (a developing solvent

ORD record

ord-737f1cddc26e4f04932710e13c1218f7

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174459B1