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With dmap; 2-chloro-1-methyl-pyridinium iodide In dichloromethane at 0℃; for 2h; |
General procedure: 2,4-Dioxo-4-phenylbutanoic acid and 4-(naphthalen-2-yl)-2,4-dioxobutanoic acid were used for the synthesis of (6-(2,4-dioxo-4-phenylbutanoyloxy)hexyl)triphenylphosphonium bromide (C23.07-TPP) and (6-(4-(naphthalen-2-yl)-2,4-dioxobutanoyloxy)hexyl)triphenylphosphonium bromide (C23.47-TPP), respectively (Supplementary Fig. 3e, f). To a stirred solution of the respective aryl-2,4-dioxobutanoic acid (about 200 mg, 1.04 mmol) and (6-hydroxyhexyl)triphenylphosphonium bromide (461 mg, 1.04 mmol) in anhydrous CH2Cl2 (15 ml) at 0 °C was added triethylamine (316 mg, 3.12 mmol), DMAP (165 mg, 1.35mmol) and 2-chloro-1-methylpyridinium iodide (319 mg, 1.25 mmol) and stirred for 2 h at 0 °C. Completion of the reaction was confirmed byTLC. The reaction mixture was diluted with cold water and the product was extracted with CH2Cl2 (20 ml × 2). The combined organic layer was washed with aqueous 1 M HCl (15 ml), aqueous NaHCO3 (15 ml) and brine (15 ml), and was then dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure, and the crude product was purified by silica gel flash chromatography (ethyl acetate/hexane) to afford the title compound (about 321 mg, 0.5 mmol) as a thick liquid. The product was confirmed by NMR and LC-MS as follows (SupplementaryFig. 3b-d):(6-(2,4-Dioxo-4-phenylbutanoyloxy)hexyl)triphenylphosphonium bromide (C23.07-TPP): 1H NMR (400 MHz, CDCl3) δ 15.29(s, 1H), 8.06-7.96 (m, 2H), 7.93-7.82 (m, 6H), 7.78 (dt, J = 7.3, 3.6 Hz, 2H),7.73-7.65 (m, 6H), 7.62 (dd, J = 10.5, 4.2 Hz, 1H), 7.52 (t, J = 7.6 Hz, 2H), 7.06(s, 1H), 4.33-4.23 (m, 2H), 4.01-3.88 (m, 2H), 1.84-1.53 (m, 6H), 1.49-1.33(m, 2H). Mass spectrometry: m/z: calcd for [C34H34O4P]+ ([M]+), 537.22; found, 537.31. |
| 0.5 mmol |
With dmap; 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere; |
General procedure: 2,4-dioxo-4-phenylbutanoic acid and 4-(naphthalen-2-yl)-2,4-dioxobutanoic acid were used for the synthesis of (6-(2,4-Dioxo-4-phenylbutanoyloxy)hexyl)triphenylphosphonium bromide (C23.07-TPP) and (6-(4-(Naphthalen-2-yl)-2,4-dioxobutanoyloxy)hexyl)triphenylphosphonium bromide (C23.47-TPP), respectively. To a stirred solution of the respective Aryl-2, 4-dioxobutanoic acid (-200 mg, 1.04mmol) and (6-hydroxyhexyl)triphenylphosphonium bromide (461 mg, 1.04 mmol) in anhydrous CH2Cb (15 mL) at 0 °C, was added tri ethyl amine (316 mg, 3.12 mmol), N,N-dimethylpyridin-4-amine (DMAP; 165 mg, 1.35 mmol), and 2-chloro-l-methylpyridinium iodide (319 mg, 1.25 mmol) respectively and stirred for 2 h at 0 °C. Completion of the reaction was confirmed by TLC. The reaction mixture was diluted with cold water and theproduct was extracted with CH2CI2 (20 mL X 2). The combined organic layer was washed with aqueous IN HC1 (15 mL), aqueous NaHCCb (15 mL), brine (15 mL), and then dried over anhydrous Na2SC>4. The solvent was evaporated under reduced pressure, and the crude product was purified by silica gel flash chromatography (Ethyl acetate / Hexane) to afford the title compound (-321 mg, 0.5 mmol) as a thick liquid. The product was confirmed by NMR and LC-MS as follows. |
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