Hydrochloric Acid → HCID 68599037, compound

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-5,6,7,8-tetrahydro-1,4-phenanthrenequinone (8.4 g, 37 mM) was dissolved in 70 ml of DMSO, and 560 g (75 mM) of LiH was gradually added thereto. The reaction solution was stirred, and after confirming no further production of hydrogen, was additionally stirred for another 30 min. Then, 12.0 g (80 mM) of prenyl bromide (1-bromo-3-methyl-2-butene) and 3.35 g (0.025 M) of LiI were gradually added thereto. The reaction solution was heated to 45° C. and then stirred vigorously for 12 hours at that temperature. The reaction solution was cooled below 10° C., and 100 ml of cold water was first added. Thereafter, 1N HCl was gradually added to maintain the resulting solution at an acidic pH>3. 200 ml of EtOAc was added to the reaction mixture which was then shaken vigorously thereafter, an organic layer was separated. The organic layer was washed with 100 ml of 5% NaHCO3, and was concentrated. The resulting concentrates purified by chromatography on silica gel to give 1.81 g (4.9 mM) of 2-Prenyl-3-prenyloxy-5,6,7,8-tetrahydro-1,4-phenanthrenequinone. The resulting was mixed with 5 ml of sulfuric acid, and the mixture was vigorously stirred at room temperature for 10 min and 20 g of ice was added thereto to complete the reaction. 60 ml of CH2Cl2 was added to the reaction materials which were then shaken vigorously. Thereafter, a CH2Cl2 layer was separated and washed with 5% NaHCO3. An aqueous layer was extracted once again using 10 ml of CH2Cl2, washed with 5% NaHCO3 and combined with the previously extracted organic layer. The organic layer was concentrated MgSO4 and the resulting concentrates purified by chromatography on silica gel to give 0.83 g (2.8 mM) of Compound 6.

Provenance & Evidence