Water → Ethyl 2-(oxan-4-ylidene)acetate

Temperature

80 °C

Triethyl phosphonoacetate (22.6 g, 99.88 mmol) was added to a solution of dihydro-2H-pyran-4(3H)-one (10.0 g, 99.88 mmol) in DMF (100 ml) at room temperature, and the mixture was stirred at 80° C. for 15 hr. The mixture was allowed to cool to room temperature, was diluted with water, and was extracted with ether. The organic layer was washed with water and saturated brine, was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5) to give the title compound as a yellow oil (13.2 g, yield 78%).

1. temperatureto cool to room temperature
2. extractionwas extracted with ether
3. washThe organic layer was washed with water and saturated brine
4. dry with materialwas dried over anhydrous magnesium sulfate
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5)

ORD record

ord-f3708654fd1d4887a32a9401cbc22bfa

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115079B2