Sodium Carbonate → HCID 59682040, compound

Participants

Reaction Steps

3,5-Diisopropyl-2-methoxymethoxy-phenyl-boronic acid (470 mg, 1.8 mmol) was dissolved in toluene (15 ml) and ethanol (15 ml). Trifluoro-methanesulfonic acid 5-acetyl-benzo[b]thiophen-3-yl ester (320 mg, 0.99 mmol), tetrakis(triphenylphosphine)palladium(0) (114 mg, 0.1 mmol) followed by some 2M sodium carbonate solution (1.98 mmol) was added to this solution. The reaction was then heated overnight, then poured into brine (20 ml) and extracted with ethyl acetate (2×20 ml). The organic layers were then dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography (chromatotron, 4μ plate, 0-10% ethyl acetate in hexanes) to give 1-[3-(3,5-diisopropyl-2-methoxymethoxy-phenyl)-benzo[b]thiophen-5-yl]-ethanone as a yellow oil (228 mg, 58%). An analytical sample was obtained by preparatory thin layer chromatography (5% ethyl acetate in hexanes). 1HNMR (250 MHz, CDCl3): δ 8.23 (s, 1H), 7.85-7.97 (m, 2H), 7.48 (s, 1H), 7.14 (d, 1H, J=1.2),7.04 (d, 1H, J=1.2),4.41 (s, 2H), 3.40 (m, 1H), 2.95 (s, 3H), 2.86 (m, 1H), 2.55 (s, 3H), 1.26 (s, 3H), 1.23 (s, 3H), 1.21, (s, 3H), 1.18 (s, 3H).

Provenance & Evidence