Potassium Fluoride → HCID 70790601, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 750 mg of 21e, 550 mg of 2-(tributylstannyl)-thiophene and 28 mg of tetrakis(triphenylphosphine)palladium(0) in 14 ml of degassed toluene was heated under N2 atmosphere for 16 hr at 110° C. The reaction mixture was cooled, 15 ml of sat. aq. KF was added, and stirring prolonged for 2 hr. The reaction was filtered through Celite, and the product was extracted with ethyl acetate. The organic layer was washed, dried and concentrated and the product purified by chromatography over silicagel (using a gradient of heptane-ethylacetate as eluent). This provided 630 mg of 21f; LC-MS-ESI: [M+1] 607.26. NMR (CDCl3) δ 7.35, 7.08, and 6.93 (3×m, 3, thienyl-H), 6.67 and 7.30 (2×s, 2, Ar—H) 5.35 (d 1, CHO), 3.95 (d, 1, CHO), 3.75 (s, 3, OCH3), 0.20 (m, 2, ethyl ester), 1.28 (t, 3, ethyl ester), 4.60, and 3.80 (2×bm, 2, CH2), 3.55 and 4.15 (2×br.m, 2, CH2), 2.92 and 3.13 (2×b.m, 2, CH2) 1.6-2.0 (bm, 4, 2×CH2), 1.32 and 1.50 (2×s, 6, dimethylketal), 1.57 (s, 9, tertC4H9).

Provenance & Evidence