Ammonium Chloride → HCID 69958142, compound

Participants

Reaction Steps

To 110.0 mg(0.50 mmol of (3S,3aS,4R,4aS,8aR,9S, 9aR)-4,9-epoxy-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one in 20 ml of dehydrated tetrahydrofuran solution were added dropwise 2.50 ml(5 equivalents) of lithium bis(trimethylsilyl)amide-tetrahydrofuran solution (1M) at −78° C. (internal temperature) under an atmosphere of argon, and the mixture was stirred for about 4 hours while raising temperature naturally. At −40° C., 2 ml of saturated aqueous solution of ammonium chloride were added, which was stirred at room temperature, and solvent was distilled off under reduced pressure. To the residue was added 10 ml of water, which was extracted with ether(5 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=2:1) to obtain 100.9 mg of (3S,3aS,4R,4aS,8aR)-4-hydroxy-3-methyl-3a,4,4a,5,6,7,8,8a-octahydronaphtho[2,3-c]furan-1(3H)-one (yield 92%).

Provenance & Evidence