Ammonium Chloride → 1-(4-Isopropyloxypyridin-2-yl)-propan-2-one

Temperature

0 °C

To a stirred solution of 4-isopropyloxy-2-methylpyridine (687 mg) in tetrahydrofuran (7 ml) was added a solution of n-butyllithium in n-hexane (1.63M, 3.34 ml) dropwise at −50° C. under a nitrogen atmosphere, and the mixture was warmed to 0° C. The mixture was cooled to −50° C., and N,N-dimethylacetamide (0.549 ml) was added dropwise. Then the mixture was warmed to room temperature, poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate (100 ml). The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 50 g, 25% ethyl acetate in n-hexane) to give 1-(4-isopropyloxypyridin-2-yl)-propan-2-one (652 mg).

1. temperatureThe mixture was cooled to −50° C.
2. temperatureThen the mixture was warmed to room temperature
3. extractionextracted with ethyl acetate (100 ml)
4. washThe organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. customevaporated under reduced pressure
7. customThe residue was purified by column chromatography (silica gel 50 g, 25% ethyl acetate in n-hexane)

ORD record

ord-3011af2c39534fe99e088b6b1340c6ef

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06521643B1