Ammonium Chloride → HCID 178431211, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 1.4 g of 1-{4-[(5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methoxy]phenyl}guanidine was dissolved in 50 ml of toluene. To the solution was added 12 ml of diisobutyl aluminum hydride (1.0 M in toluene) and the mixture was stirred at room temperature for 14 hours. After further addition of 6 ml of diisobutyl aluminum hydride (1.0 M in toluene) at room temperature, the mixture was heated under reflux for 2 hours. After reaction, a saturated aqueous ammonium chloride solution was added, and insoluble matters were filtered off on Celite and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography eluting with chloroform containing 10% methanol to give 0.67 g of 1-{4-[(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)methoxy]phenyl}guanidine as a pale yellow oil (yield 52%).

Provenance & Evidence