Tetrahydrofuran → HCID 22915773, compound

Into a three-necked flask equipped with a dropping funnel, a three-way cook and a thermometer was placed 2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide (9.1 g, 20 mmols), followed by adding tetrahydrofuran (100 ml), suspending, stirring under ice cooling till the liquid temperature reached 10° C. The resulting reaction mixture was added potassium t-butoxide (2.2 g, 20 mmols) followed by elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (50 ml) solution of 4-(3-fluoro-4-trifluoromethoxyphenyl)cyclohexanone (5.5 g, 20 mmols) over 30 minutes from the dropping funnel, further stirring the reaction mixture for 5 hours after completion of the dropwise addition, adding ether (100 ml), allowing to stand for one hour, filtering off deposited insoluble substance, concentrating the filtrate under reduced pressure, and isolating and purifying the resulting pale brown oil by means of silica gel column chromatography, to obtain 1-(2-(1,3-dioxan-2-yl)ethylidene)-4-(3-fluoro-4-trifluoromethoxyphenyl)cyclohexane.

1. customInto a three-necked flask equipped with a dropping funnel
2. customreached 10° C
3. customThe resulting reaction mixture
4. customup to room temperature
5. customfor one hour
6. stirringstirring for one hour
7. stirringfurther stirring the reaction mixture for 5 hours
8. additionafter completion of the dropwise addition
9. filtrationfiltering off
10. concentrationconcentrating the filtrate under reduced pressure
11. customisolating
12. custompurifying the resulting pale brown oil by means of silica gel column chromatography

ORD record

ord-a4ab46ba8619492eb98683363652c4eb

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05662830