Ethyl formate → HCID 86670261, compound

Temperature

-78 °C

In a dehydrated tetrahydrofuran (20 ml) solution of (4-chloro-phenyl)-[6-isopropylidene-tetrahydro-thiopyran-2-ylidene]-amine (1.1 g), 3.6 ml of lithium diisopropylamide (1.5 mol/l, tetrahydrofuran/cyclohexane solution) was added dropwise at −78° C. under a nitrogen atmosphere. After stirring at −78° C. for 30 minutes, a tetrahydrofuran (2 ml) solution of ethyl formate (0.39 g) was added dropwise. After raising the temperature to room temperature and further stirring for 1 hour, an aqueous saturated ammonium chloride solution was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.45 g of the target compound.

1. temperatureAfter raising the temperature to room temperature
2. stirringfurther stirring for 1 hour
3. extractionthe reaction mixture was extracted with ethyl acetate
4. washThe organic layer was washed with a saturated saline solution
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography

ORD record

ord-f7d3f54b0d3e400bae81713a702bade0

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012493B2