Diethylamine → 2,2-Diethyl-4-methoxy-1a,2,7,7a-tetrahydro-1H-naphtho[2,3-b]azirene

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,1-Diethyl-7-methoxy-3,4-dihydro-1H-naphthalen-2-one oxime (4.68 g, 18.96 mmol) in dry THF (100 mL) at 0° C. was added the diethylamine (4.9 mL, 47.4 mmol) and the LAH (95% powder) (2.16 g, 56.9 mmol). The mixture was stirred at 0° C. for min then heated to reflux for 3 h. The gray solution was cooled down to 0° C., quenched with brine and diluted with AcOEt. The organic layer was decanted, washed with H2O (2×), brine, dried over MgSO4, filtered then evaporated. The residue was purified by a flash chromatography (3% MeOH/CH2Cl2) (3.889 g, 89%).

Provenance & Evidence