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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information