Benzenesulfonyl chloride → 7-Oxocyclohepta-1,3,5-trien-1-yl benzenesulfonate

Participants

Reaction Steps

2-Hydroxycyclohepta-2,4,6-trienone (0.2 g, 1.7 mmol) was reacted with benzenesulfonyl chloride (0.63 mL, 4.9 mmol) in 5 mL of pyridine to afford PZBG-4a in 76% yield (0.33 g, 1.3 mmol). 1H NMR (400 MHz, DMSO) δ=7.95 (d, J=7.6 Hz, 2H), 7.80 (t, J=7.6 Hz, 1H), 7.67 (t, J=8 Hz, 2H), 7.43-7.37 (m, 2H), 7.25 (t, J=8.4 Hz, 1H), 7.14-7.09 (m, 2H). 13C NMR (100 MHz, CDCl3) δ=179.24, 154.79, 141.19, 138.21, 136.37, 136.33, 135.57, 131.96, 130.92, 130.27, 128.76. ESI-MS(+): m/z 262.97 [M+H]+, 279.72 [M+NH4]+, 284.99 [M+Na]+.

Provenance & Evidence