Sodium hydride → HCID 66671460, compound

Participants

Reaction Steps

6-Methoxy-3,4-dihydroisoquinolin-1(2H)-one (1.0 g, 5.64 mmol) was dissolved in N,N-dimethylformamide (15 mL), (3-bromopropoxy)(tert-butyl)dimethylsilane (2.62 mL, 11.3 mmol) and 55% sodium hydride (259 mg, 5.93 mmol) were added under ice cooling, and the mixture was stirred at room temperature under a nitrogen atmosphere for 2 hours. After the reaction was completed, saturated aqueous ammonium chloride was added to the reaction mixture under ice cooling, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (5 mL), a 1.0 M tetrabutylammonium fluoride-tetrahydrofuran solution (22.5 mL, 22.5 mmol) was added under ice cooling, and the mixture was stirred at room temperature under a nitrogen atmosphere for 2 hours. After the reaction was completed, saturated aqueous ammonium chloride was added to the reaction mixture under ice cooling, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol, 10:1, v/v) to give the title compound (1.93 g; yield, 100%) as a colorless oily substance.

Provenance & Evidence