Pyridine → HCID 16040662, compound

Reaction equation

[OH:1][C:2]1[C:3](=[O:21])[CH:4]=[C:5]([OH:20])[C:6](=[O:19])[C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:28]1([CH3:37])[CH:33]=[CH:32][CH:31]=[C:30]([C:34](Cl)=[O:35])[CH:29]=1>ClCCl>[CH3:23][C:24]1[CH:6]=[C:7]([C:2]([O:19][C:6]2[C:5](=[O:20])[CH:4]=[C:3]([O:21][C:34]([C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([CH3:37])[CH:29]=3)=[O:35])[C:2](=[O:1])[C:7]=2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:1])[CH:27]=[CH:26][CH:25]=1

Participants

Procedure

To a stirred solution of 2,5-dihydroxy-3-undecyl-1,4-benzoquinone (0.5 g, 1.7 mmole) in dichloromethane (20 mL) was added pyridine (0.55 mL, 6.8 mmole). To this, was added 3-toluoyl chloride (0.654 gm, 4.25 mmole) at 15-20° C. and stirred, allowed to attain 30° C. and stirring was continued for 3 h (TLC). The organic layer was extracted with dichloromethane, washed (water, brine), dried (Na2SO4), concentrated to crude which was purified by SiO2 column chromatography (10-20% EtOAc in hexane) to pure mass (0.64 g, 71%).