2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19816653, compound

Participants

Reaction Conditions

Reaction Steps

123 mg of 9-deoxypodophyllol was dissolved in 18 mL of dry methylene chloride, and a solution of 82 mg of 2,3-dichloro-5,6-dicyanobenzoquinone in 2.7 mL of dry methylene chloride was added. The mixture was stirred at 22° C. in an atmosphere of dry nitrogen for 20 hours. Thereafter, the reaction mixture was processed in the manner described in Example 5 using volumes of extraction solvents, reagents, water, and brine in proportion to the amounts of starting diol and oxidizing agent used in this example. The resulting residue after processing was chromatographed on a silica gel plate (GF, 20×20 cm, 500μ), whereby distilled acetone was used as the developing solvent. Removal of the major band from the plate followed by separation of the major product from the silica gel by extraction of the latter with distilled acetone gave the pure oxabicylooctane derivative having a melting point of 148-149° C. and an optical rotation of [α]25D =+44.2 (acetone, c 1.19). HRMS Calcd. For C22H24O7: 400.1522, Found: 400.1526.

Provenance & Evidence