関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dichloromethane | HCID 6344 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | Methyl 11-bromoundecanoate | HCID 223913 | — |
| 反応物 | HCID 178418634 | HCID 178418634 | — |
| 触媒 | Trioctylmethylammonium chloride | HCID 21218 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | 2,2,4-Trimethylpentane | HCID 10907 | — |
| 生成物 | Methyl 11-thioacetylundecanoate | HCID 20195807 | 94.3% |
反応手順
Compound 103 (17.8 g, 64 mmol), thioacetic acid (9.7 g, 9.0 ml, 128 mmol), methyltrioctylammonium chloride (0.5 g), cesium carbonate (25 g, 77 mmol), dichloromethane (95 ml) and water (95 ml) were stirred at room temperature for 15 h. The reaction was monitored by TLC (SiO2, ethyl acetate:isooctane, 1:5). The mixture was extracted with dichloromethane and the combined extracts were dried (Na2SO4) and concentrated. Distillation gave pure 104 (15.6 g, 89%) with b.p. 137°-139° (0.1 torr) and m.p. <25° (from isooctane). 1H-NMR (CDCl3, Me4Si) δ 3.67 (s, 3H, MeO), 2.86 (t, 2H, J=7.1 Hz, S--CH2), 2.32 (s, 3H, MeCO), 2.30 (t, 2H, J=7.7 Hz, CH2CO). 13C-NMR (CDCl3, Me4Si) δ 195.9, 174.1 (CO), 51.3, 34.0, 30.5, 29.4, 29.3, 29.2, 29.1, 29.0, 28.9, 28.7, 24.8.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US04675392 |
|---|
| 出典データセット | uspto-grants-1987_06 |
|---|
| ORD ID | ord-3528f137b40f4eca9c0a965cf04714e1 |
|---|
| 出典メモ | uspto-grants-1987_06 |
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