(E)-1,3-Dichloropropene → (E)-2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(3-chloroprop-2-enyloxy)pyridine

A mixture of 6-hydroxy-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methylpyridine (0.9 g, 3.3 mmol) and NaH (60 % in oil, 0.16 g, 4 mmol) in acetonitrile (20 ml) and DMF (1 ml) is stirred for 10 min at ambient temperature and (E)-1,3-dichloropropene (0.4 g, 3.6 mmol) is added. After stirring for 60 h at ambient temperature, the remaining NaH is deactivated and the resulting mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v) yields the title compound (0.6 g, 52 % yield) as an colorless oil.

1. stirringAfter stirring for 60 h at ambient temperature
2. filtrationfiltered through a bed of silica gel
3. washThe filtrate is washed with water
4. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
5. filtrationfiltered
6. customevaporated in vacuo
7. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

ORD-Eintrag

ord-34dd5c0c7f8a40b59706a99c17232257

Quelldatensatz

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06130188