Diisopropylamine → HCID 117759689, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a hexane solution (1.6 M, 29.5 mL) of n-butyllithium was added to a solution of diisopropylamine (6.60 mL) in THF (80 mL) at −15° C., and the mixture was stirred at −15° C. for 5 min. A solution of 5-fluoro-2-methoxypyridine (5.00 g) in THF (30 mL) was added dropwise to the reaction mixture at −78° C. over 15 min, and the mixture was stirred at −78° C. for 1.5 hr. A solution of cyclopropanecarbaldehyde (3.53 mL) in THF (15 mL) was added dropwise to the reaction mixture at −78° C. over 20 min, and the mixture was stirred at −78° C. for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product (8.87 g) of the title compound as a pale-yellow oil. This compound was used for the next step without further purification.

Provenance & Evidence