Toluene → HCID 69367872, compound

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Reaction Steps

A solution of 2,2,2-trifluoro-N-(2-iodo-5-methoxy-phenyl)-acetamide 76b (4.6 g, 13.3 mmole) and methyl (triphenylphosphoranylidene)acetate (8.7 g, 25 mmole) in 50 ml toluene was brought to reflux for 5 hours and cooled to room temperature. The solution was concentrated, in vacuo and purified by column chromatography (eluting with 2-6% EtOAc in hexanes) to give 4.8 g product (87% yield). 1H NMR (300 MHz, CDCl3) δ9.57 (1H, s), 7.68 (1H, d, J=8.8 Hz), 6.83 (1H, d, J=2.8 Hz), 6.57 (1H, dd, J=2.8, 8.8 Hz), 5.43 (1H, s), 4.23 (2H, m), 3.76 (3H, s), 1.55 (3H, s), 1.31 (3H, m).

Provenance & Evidence