Ammonium Chloride → HCID 15427655, compound

Participants

Reaction Steps

To 9.96 g(5 equivalents) of methyltriphenylphosphonium iodide in 400 ml of dehydrated ether suspension were added dropwise 4.1 ml(5 equivalents) of sodium bis(trimethylsilyl)amide-toluene solution(0.60M) under cooling with ice and under an atmosphere of argon. After stirring for 1 hour at room temperature, 1.17 g of (1S,3S,3aR,4aS,8aR,9aS)-1-methoxy-3-methyl-4-oxo-dodecahydronaphtho[2,3-c]furan(4.93 mmol) in 30 ml of dehydrated ether solution were added dropwise again under cooling with ice. After stirring for 2 hours at room temperature, 50 ml of cold saturated aqueous solution of ammonium chloride were added to the reaction mixture and solvent was distilled off. To the residue were poured 100 ml of saturated brine, which was extracted with ether(50 ml×3). The organic layer was dried over anhydrous magnesium sulfate, filtered and solvent was distilled off. The residue was purified by means of silica gel column chromatography(hexane:ethyl acetate=10:1) to obtain 1.0 g of (1S,3S,3aS,4aS,8aR,9aS)-1-methoxy-3-methyl-4-methylene-dodecahydronaphtho[2,3-c]furan (yield 86%).

Provenance & Evidence