2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 12000074, compound

Participants

Reaction Steps

To a solution of methyl (R)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy]-propanoate (10) (9.00 mg, 14.7 μmol, 1.00 eq.) in dichloromethane (2.00 mL) and phosphate buffer (0.20 mL, pH=7) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5.00 mg, 22.1 μmol, 1.50 eq.) at 5° C. After being stirred at the same temperature for 1 h, the reaction mixture was diluted with dichloromethane and treated with saturated aq. NaHCO3 at 0° C. The reaction mixture was extracted with two portions of dichloromethane. The combined extract was washed with saturated aq. NaHCO3, brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane:diethyl ether=89:11) to give methyl (R)-3-hydroxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy]-propanoate (11) (4.10 mg, 8.89 μmol, 61%) as a colorless oil and recover (10) (3.10 mg, 5.12 μmol, 34%).

Provenance & Evidence