2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 71679545, compound

Participants

Reaction Steps

6,7-dimethoxy-2-(4-methyl-2(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl)-1,2,3,4-tetrahydroisoquinoline (Formula 5; 18.4 mg, 0.0693 mmol) and a 4 Å molecular sieve (100 mg) were put into anhydrous CH2Cl2 (0.5 mL) and stirred. A solution obtained by dissolving 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ; 19.3 mg, 0.104 mmol) and LiClO4 (2.19 mg, 0.0208 mmol) in anhydrous CH2Cl2 (0.5 mL) in a separate container was slowly added to the reaction solution and stirred for 20 min. A saturated NaHCO3 aqueous solution (1 mL) was added thereto to complete the reaction. An organic layer was extracted, and then the organic layer collected was washed with distilled water and a brine solution. Anhydrous magnesium sulfate was used to dry the organic layer, filtration under reduced pressure and evaporation under reduced pressure were performed, and then column chromatography was used to obtain 8.22 mg (yield 55%) of the title compound.

Provenance & Evidence