Dichloromethane → HCID 22467324, compound

Participants

Reaction Steps

To a solution of 1-aminomethyl-5-(tert-butyldiphenyl-silyloxy)-1,2,3,4-tetrahydronaphthalen-1-ol (34.5 g) in 20% AcOH (700 ml) was added NaNO2 (7.18 g) in water (60 ml) at 5° C. The mixture was stirred at the same temperature for 2.5 hours. After addition of CH2Cl2 (70 ml), the mixture was stirred for 30 minutes. The reaction mixture was extracted with EtOAc. The organic layer was washed with water and then brine. It was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (hexane-EtOAc 10:1) to give 1-(tert-butyldiphenylsilyloxy)-6,7,8, 9-tetrahydro-5H-benzocyclohepten-6-one (12.52 g).

Provenance & Evidence