Butyl iodide → 1-Butyl-3-methoxy-2-pyridone

To a solution of 3-methoxy-2(1H)-pyridone (2-034-01) (5.0 g) in DMF (40 mL) was added sodium hydride (60% wt, 2.2 g) at room temperature. After the reaction mixture was stirred for 20 min, 1-iodobutane (15.5 g) was added to the reaction mixture, and the reaction mixture was stirred for 40 min. After the reaction was quenched with water, the solvent was removed. To the residue were added a saturated aqueous solution of ammonium chloride and ethyl acetate, and the organic layer was separated, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed water and brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (toluene/acetone=4/1) to give 1-butyl-3-methoxy-2-pyridone (2-034-02) (6.7 g, 93%) as an oil.

1. customat room temperature
2. stirringthe reaction mixture was stirred for 40 min
3. customAfter the reaction was quenched with water
4. customthe solvent was removed
5. additionTo the residue were added a saturated aqueous solution of ammonium chloride and ethyl acetate
6. customthe organic layer was separated
7. extractionthe aqueous layer was extracted three times with ethyl acetate
8. washThe combined organic layers were washed water and brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customevaporated under reduced pressure
11. customThe crude product was purified by silica gel column chromatography (toluene/acetone=4/1)

ORD record

ord-c42cc50c11744aa39c52737608db2efe

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088924B2