関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 2-Iodobenzylic alcohol | HCID 107629 | — |
| 反応物 | HCID 178418936 | HCID 178418936 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | (2-(2H-1,2,3-Triazol-2-YL)phenyl)methanol | HCID 67251671 | 130% |
反応手順
To a mixture of (2-iodophenyl)methanol [5159-41-1] (1.50 g, 6.41 mmol), 1H-1,2,3-triazole (0.797 g, 11.54 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine [68737-65-5] (0.091 g, 0.641 mmol) and Cs2CO3 (3.76 g, 11.54 mmol) in DMF (15 mL), CuI (0.61 g, 3.20 mmol) was added and the reaction mixture was stirred for 20 min at 120° C. and 15 min at 160° C. in the microwave. The reaction mixture was cooled to rt and filtered to remove the solids. The filtrate was concentrated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane) to yield the title compound (1.46 g, 64%). [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.10 (s, 2H), 7.74 (d, J=7.53 Hz, 1H), 7.61 (dd, J=8.03, 1.25 Hz, 1H), 7.52 (td, J=7.53, 1.25 Hz, 1H), 7.44 (m, 1H), 5.26 (t, J=5.40 Hz, 1H), 4.59 (d, J=5.02 Hz, 2H); LCMS RtA=0.68, [M+H]+=176.1].
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08530648B2 |
|---|
| 出典データセット | uspto-grants-2013_09 |
|---|
| ORD ID | ord-e73e2ef4f7bb44c99e97196b1224ac4c |
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| 出典メモ | uspto-grants-2013_09 |
|---|
