Triethylamine → Methyl 1-benzyl-4-formyl-5-(3-hydroxy-3,3-diphenylprop-1-ynyl)-1H-pyrrole-2-carboxylate

참여 물질

반응 단계

A solution of 5 (0.47 g, 1.3 mmol), 1,1-diphenylprop-2-yn-1-ol (0.66 g, 3.2 mmol), CuI (0.05 g, 0.3 mmol), Pd(PPh3)2Cl2 (0.18 g, 0.3 mmol), PPh3 (0.07 g, 0.3 mmol), and Et3N (4 mL) in anhydrous DMF (4 mL) was stirred for 16 hours at 70° C. under N2 atmosphere. The reaction mixture was then partitioned between water and EtOAc. The combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 6 as a pale yellow solid (0.49 g, 87%). 1H NMR (CDCl3) δ 9.88 (s, 1H), 7.50-7.52 (m, 4H), 7.36 (s, 1H), 7.24-7.30 (m, 8H), 7.04 (m, 2H), 5.69 (s, 2H), 3.80 (s, 3H), and 3.65 (s, 1H); 13C NMR (CDCl3) δ 185.16, 160.72, 144.07, 136.84, 128.91, 128.72, 128.33, 127.91, 127.79, 127.05, 126.23, 124.96, 116.97, 103.35, 75.37, 75.27, 52.15, and 50.38.

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