Diisopropylamine → HCID 44597011, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (12.6 mL, 89.9 mmol) in anhydrous THF (50 mL) is added n-butyllithum (42.2 mL of an 1.6M in hexane) dropwise at 0° C. After 30 min at 0° C., 2-fluoro-4-methylpyridine (5 g, 45 mmol) is added. The resulting mixture is stirred at 0° C. for 30 min. After the addition of methyl isobutyrate (5.4 mL, 47.3 mmol) at 0° C., the reaction mixture is stirred overnight. The reaction mixture is quenched with acetic acid at 0° C., diluted with water, and extracted with ethyl ether. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc/heptane 7:93 to 60:40) to give 4.8 g of 1-(2-fluoro-pyridin-4-yl)-3-methyl-butan-2-one as a light yellowish solid.

Provenance & Evidence