Hydrochloric Acid → HCID 87516624, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4bromo-1-p-methoxyphenylsulfonyl-2-(3,4,5-trimethoxyphenyl)-pyrrole (0.30 g, 0.62 mmol, Example 94b) in ethyl ether/THF (5 ml, 1:1 v/v) tert-butyl-lithium (1.5 equiv., 1.7 M in pentane) is added at −78° C. The reaction mixture is stirred for 20 min at −78° C., and DMF (255 mg, 5 equiv.) is added drop wise. The reaction mixture is kept for 1 h at −78° C., allowed to come to 4° C., and poured onto ice, 1 M aqueous HCl and ethyl acetate. The organic layer is dried (MgSO4), the solvents are evaporated, and the residue chromatographed on SiO2 with ethyl acetate/hexane to yield the title compound (0.196 g, 73%) as a light yellow solid. 1H-NMR (300 MHz, DMSO-d6): 9.86 (s, CHO); 8.44 (d, J=1.9, 1H); 7.38 (d, J=9.0, 2H); 7.01 (d, J=9.0, 2H); 6.56 (d, J=1.9, 1H); 6.36 (s, 2H); 3.82 (s, MeO); 3.72 (s, MeO); 3.67 (s, 2MeO).

Provenance & Evidence