Diisopropylamine → HCID 52951617, compound

Participants

Reaction Steps

n-BuLi in hexane (1.6 M, 7.6 mL, 11.9 mmol) was added dropwise to a solution of diisopropylamine (1.089 g, 10.9 mmol) in THF (25 mL) at −60 to −70° C. under N2. The mixture was stirred for 10 min. A solution of 5-methoxy-2-methyl-pyridine (1.274 g, 10.35 mmol) in THF (5 mL) was added dropwise to the above mixture. Stirring was continued for another 10 min and 3,4,5-trimethoxybenzonitrile (1.88 g, 9.74 mmol) in THF (5 mL) was added at −70° C. The mixture was stirred at −78° C. for 1 h and then allowed to warm to room temperature. Stirring was continued for another 2 h and the reaction mixture was poured into an ice-cold aqueous NH4Cl solution. The organic layer was separated and the aqueous phase was extracted with ether. The combined organic layers were extracted with a dilute HCl solution. The aqueous layer was washed with ether, neutralized with 10% aqueous NaOH, and extracted with ether. The organic layer was washed with water and dried. The residue was purified by chromatography eluting with CH2Cl2 to give 2-(5-methoxypyridin-2-yl)-1-(3,4,5-trimethoxyphenyl)ethanone (2.31 g, 75.0%).

Provenance & Evidence