HCID 54057319, compound → HCID 53747219, compound

Participants

Reaction Steps

A solution of 1.00 g (2.79 mmol) of 2-ethoxycarbonyl-1-methyl-4-[2-(3-oxapropyloxy)-5-methoxyphenyl]propenylpyrrole in 5 ml of 1:1 aqueous trifluoroacetic acid was stirred at 0° for 1 hour, then at room temperature for 1 hour. The solution was partitioned between ether and water and the ether layer was washed with 3 portions of water. The ether extract was dried (Na2SO4), concentrated, and chromatographed on silica using 20% ethylacetatehexane to afford 0.68 g (77%) 2-ethoxycarbonyl-1-methyl-4-(2-hydroxy-5-methoxyphenyl)propenylpyrrole of a colorless glass. NMR (CDCl3) δ1.30 (t, 3H, J=6 Hz), 3.4 (trans), 3.65 (cis) (d, total 2H, J=6 Hz, trans:cis=10:1), 3.78 (s, 3H), 3.90 (s, 3H), 4.25 (q, 2H, J=6 Hz), 5.75-6.6 (m, 2H), 6.7-7.3 (m, 5H).

Provenance & Evidence