HCID 44818468, compound → 4-Pyridinylacetone

Temperature

0 °C

To a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of argon, was added THF (70 mL) and N-methoxy-N-methyl-2-(pyridin-4-yl)acetamide (7.0 g, 0.039 mol, 1.0 equiv). The mixture was cooled to 0° C. and CH3MgBr (3M in THF, 65 mL, 5.0 equiv) was added dropwise. The resulting solution was warmed to ambient temperature and stirred for 16 h. The reaction mixture was cooled to 0° C. and quenched by the addition of saturated NH4Cl (aq, 100 mL). The resulting solution was extracted with EtOAc (3×200 mL). The organic layers were combined, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified by flash chromatography (silica gel, CH2Cl2/CH3OH (20:1)) to yield 2.7 g (51%) of the title compound as yellow oil. 1H-NMR (400 MHz, CDCl3): δ ppm 8.58 (m, 2H), 7.17 (d, J=0.4 Hz, 2H), 3.75 (s, 2H), 2.24 (s, 3H).

1. customTo a 250-mL 3-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of argon
3. temperatureThe resulting solution was warmed to ambient temperature
4. temperatureThe reaction mixture was cooled to 0° C.
5. customquenched by the addition of saturated NH4Cl (aq, 100 mL)
6. extractionThe resulting solution was extracted with EtOAc (3×200 mL)
7. dry with materialdried over anhydrous Na2SO4
8. concentrationconcentrated under reduced pressure
9. customThe crude was purified by flash chromatography (silica gel, CH2Cl2/CH3OH (20:1))

ORD record

ord-c2dc55236b1941b39d44827011b1570f

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181200B2