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

Temperature

-30 °C

Under nitrogen gas stream, a mixture of 1330 g (2930 mmol) of 2-(1,3-dioxane-2-yl)ethyltriphenylphosphonium bromide with 6.0 l of THF was cooled down to −30° C., and 303 g (2700 mmol) of t-BuOK was added thereto and stirred for 1 hour. To this mixture was added by drops a solution of 500 g (2250 mmol) of 4-(trans-4-propylcyclohexyl)cyclohexanone in 3.0 l of THF while being maintained at a temperature lower than −30° C. After finishing of the adding, the reaction temperature was gradually raised up to room temperature and they were stirred for further 5 hours. The reaction mixture was filtered with Celite, the solvent was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: mixed solvent of toluene/ethyl acetate=9/1) to obtain 652 g of a crude 2-(2-(4-(trans-4-propylcyclohexyl)cyclohexylidene)-ethyl-1,3-dioxane.

1. temperaturewhile being maintained at a temperature lower than −30° C
2. temperaturethe reaction temperature was gradually raised up to room temperature and they
3. stirringwere stirred for further 5 hours
4. filtrationThe reaction mixture was filtered with Celite
5. distillationthe solvent was distilled off under a reduced pressure
6. additionthe residue was subjected to silica gel column chromatography (eluent: mixed solvent of toluene/ethyl acetate=9/1)

ORD record

ord-c07abed4bfa04c2bb79183851028d825

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458433B1