関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | 4-Cyanophenylboronic acid | HCID 2734326 | — |
| 反応物 | 2-Bromo-3-methyl-2-cyclopenten-1-one | HCID 4437009 | — |
| 触媒 | 1,5-Diphenylpenta-1,4-dien-3-one;palladium | HCID 154270 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | Ethanol | HCID 702 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | 4-(2-Methyl-5-oxo-1-cyclopenten-1-yl)benzonitrile | HCID 21986159 | — |
反応手順
2-Bromo-3-methyl-cyclopent-2-enone (Intermediate TEN1) (commercially available from Aldrich) (2.04 g, 11.4 mmol) and K2CO3 (3.16 g in 11 mL H2O) in toluene (45 mL) was treated with a solution 4-cyanophenylboronic acid (commercially available from Aldrich) (2.2 g, 15 mmol) in EtOH (27 mL). Tetrakis(triphenylphosphine) palladium(0) Pd(PPh3)4 (0.4 g), bis(dibenzylideneacetone) palladium(0), Pd2(dba)3 (0.055 g, ˜5 mol %) and triphenylphosphine (0.4 g) were added and the mixture was purged with N2 for 15 m. The mixture was heated to 80° C. for 15 h. The mixture was diluted with water and EtOAc:hexane. After extracting with EtOAc:hexane, the combined organic layers were dried over MgSO4, filtered and evaporated to dryness. The crude oil was purified by column chromatography on silica gel with CH2Cl2 to give 4-(2-methyl-5-oxo-cyclopent-1-enyl)-benzonitrile (Intermediate TEN2) 1.74 g.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08071635B2 |
|---|
| 出典データセット | uspto-grants-2011_12 |
|---|
| ORD ID | ord-bb988a6eaad74860aad1d0206028cbfb |
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| 出典メモ | uspto-grants-2011_12 |
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