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【结 构 式】 
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【分子编号】46053 【品名】4-hydroxy-2-butanone 【CA登记号】 |
【 分 子 式 】C4H8O2 【 分 子 量 】88.10632 【元素组成】C 54.53% H 9.15% O 36.32% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of 2-bromo-6-methoxynaphthalene (I) with 3-buten-2-one (II) by means of PdCl2, PPh3 and K2CO3 in DMF at 132 C gives 4-(6-methoxy-2-naphthyl)-3-buten-2-one (III), which is then hydrogenated with H2 over Pd/C in DMF. The same condensation can be performed with PdCl2 , PPh3 and NaHCO3 in 1-methyl-2-pyrrolidone at 130 C. The reaction of 4-hydroxy-2-butanone (IV) with acetic anhydride or acetyl chloride gives 4-acetyl-2-butanone (V), which is condensed with 2-bromo-6-methoxynaphthalene (I) by means of PdCl2, PPh3 and K2CO3 in DMF at 132 C to yield the previously reported 4-(6-methoxy-2-naphthyl)-3-buten-2-one (III).
| 【1】 Aslam, M.; et al.; Convenient synthesis of nabumetone. Synthesis 1989, 869. |
| 【2】 Fritch, J.R.; Rios, D.E.; Smith, J.C.; Aslam, M. (Celanese AG); Use of 4-substd. 2-butanones to prepare nabumetone. WO 9640608 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 44399 | 2-bromo-6-methoxynaphthalene; 6-bromo-2-naphthyl methyl ether | 5111-65-9 | C11H9BrO | 详情 | 详情 |
| (II) | 30324 | 3-buten-2-one; methyl vinyl ketone | 78-94-4 | C4H6O | 详情 | 详情 |
| (III) | 32194 | (E)-4-(6-methoxy-2-naphthyl)-3-buten-2-one | C15H14O2 | 详情 | 详情 | |
| (IV) | 46053 | 4-hydroxy-2-butanone | C4H8O2 | 详情 | 详情 | |
| (V) | 46054 | 3-oxobutyl acetate | C6H10O3 | 详情 | 详情 |