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Triphenylphosphine → N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | 3-Hydroxyacetanilide | HCID 12124 | — |
| 反応物 | 3-Methyl-3-buten-1-ol | HCID 12988 | — |
| 反応物 | Diethyl azodicarboxylate | HCID 5462977 | — |
| 反応物 | Acetic acid 3-formylamino-phenyl ester | HCID 57470213 | — |
| 溶媒 | Benzene | HCID 241 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide | HCID 57567384 | 52% |
反応手順
A suspension of the mixture of N-(3-hydroxy-phenyl)-acetamide and acetic acid 3-formylamino-phenyl ester (18.12 g, 0.12 mol), 3-methyl-but-3-en-1-ol (8.6 g, 0.1 mol), DEAD (87 g, 0.2 mol) and Ph3P (31.44 g, 0.12 mol) in benzene (250 mL) was heated at reflux overnight and then cooled to room temperature. The reaction mixture was poured into water and the organic layer was separated. The aqueous phase was extracted with EtOAc (300×3 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give N-[3-(3-methyl-but-3-enyloxy)-phenyl]-acetamide (11 g, 52%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08101767B2 |
| 出典データセット | uspto-grants-2012_01 |
| ORD ID | ord-021becc2882647d9a3eeac70fe12e297 |
| 出典メモ | uspto-grants-2012_01 |