HCID 21288120, compound → HCID 54057319, compound

Participants

Reaction Steps

A solution of 1.6M n-butyllithium (4.0 ml, 6.0 mmol) was added to a suspension of 3.45 g (5.90 mmol) of 2-[2-(3-oxapropyloxy)-5-methoxyphenyl]ethyltriphenylphosphonium iodide in 20 ml of dry tetrahydrofuran at 0°. After 30 minutes a solution of 1.10 g (6.07 mmol) of 2-ethoxycarbonyl-1-methylpyrrole-2-carboxaldehyde in 5 ml of dry tetrahydrofuran was added and the solution was stirred for 30 minutes. The mixture was partitioned between ether and water and the ether layer was washed with water, dried (Na2SO4) and evaporated. The residue was chromatographed on silica using 20% ethylacetatehexane to afford 1.78 g (85%) of 2-ethoxycarbonyl-1-methyl-4-[2-(3-oxapropyloxy)-5-methoxyphenyl]propenylpyrrole as a colorless glass. NMR (CDCl3) δ1.30 (t, 3H, J=6 Hz), 3.40 (s, 3H), 3.45 (trans), 3.70 (cis) (d, J=6 Hz, total 2H, cis:trans, 1:10), 3.78 (s, 3H), 3.90 (s, 3H), 4.25 (q, 2H, J=6 Hz), 5.0 (trans), 5.05 (cis) (s, total 2H), 5.75-6.6 (m, 2H), 6.7-7.3 (m, 5H).

Provenance & Evidence