ethyl 2-[(6-methoxy-2-naphthyl)methyl]-3-oxobutanoate -Drug Synthesis Database

【结构式】

【分子编号】29958

【品名】ethyl 2-[(6-methoxy-2-naphthyl)methyl]-3-oxobutanoate

【CA登记号】

【分子式】C₁₈H₂₀O₄

【分子量】300.3544

【元素组成】C 71.98% H 6.71% O 21.31%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

The condensation of 6-methoxy-2-naphthaldehyde (I) with ethyl aceto-acetate (II) gives ethyl 2-(6-methoxy-2-naphthylmethylene)acetoacetate (III), which is reduced to ethyl 2-(6-methoxy-2-naphthylmethyl)acetoacetate (IV). Finally, this compound is hydrolyzed and decarboxylated in acidic medium.

参考文献中间体

合成目标

【1】 Rose, C.J.; Miller, D. (SmithKline Beecham plc); A1 14777 by hydrogenation. CA 1134384 .

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)	29956	6-Methoxy-2-naphthaldehyde	3453-33-6	C₁₂H₁₀O₂	详情	详情
(II)	11819	ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate	141-97-9	C₆H₁₀O₃	详情	详情
(III)	29957	ethyl (Z)-2-acetyl-3-(6-methoxy-2-naphthyl)-2-propenoate		C₁₈H₁₈O₄	详情	详情
(IV)	29958	ethyl 2-[(6-methoxy-2-naphthyl)methyl]-3-oxobutanoate		C₁₈H₂₀O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

The bromination of beta-naphthol (I) gives the 1,6-dibromo-beta-naphthol (II), which is partially debrominated with Sn and BrH, yielding 1-bromo-beta-naphthol (III). The methylation of (III) with methanol/sulfuric acid affords the corresponding methyl ether (IV), which is treated with Mg and DMF to provide 6-methoxynaphthalene-2-carbaldehyde (V). The condensation of (V) with ethyl acetoacetate (VI) gives the expected adduct (VII), which is reduced with H2 over Pd/C to provide 2-acetyl-3-(6-methoxy-2-naphthyl)propionic acid ethyl ester (VIII). Finally, this compound is decarboxylated with aqueous HCl.

参考文献中间体

合成目标

【1】 Zhang, G.; et al.; A study on the synthesis of a new anti-inflammatory agent - nabumetone. J Shenyang Coll Pharm 1988, 5, 4, 259.

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)	44396	2-naphthol	135-19-3	C₁₀H₈O	详情	详情
(II)	44397	1,6-dibromo-2-naphthol	16239-18-2	C₁₀H₆Br₂O	详情	详情
(III)	44398	6-bromo-2-naphthol	15231-91-1	C₁₀H₇BrO	详情	详情
(IV)	44399	2-bromo-6-methoxynaphthalene; 6-bromo-2-naphthyl methyl ether	5111-65-9	C₁₁H₉BrO	详情	详情
(V)	29956	6-Methoxy-2-naphthaldehyde	3453-33-6	C₁₂H₁₀O₂	详情	详情
(VI)	11819	ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate	141-97-9	C₆H₁₀O₃	详情	详情
(VII)	29957	ethyl (Z)-2-acetyl-3-(6-methoxy-2-naphthyl)-2-propenoate		C₁₈H₁₈O₄	详情	详情
(VIII)	29958	ethyl 2-[(6-methoxy-2-naphthyl)methyl]-3-oxobutanoate		C₁₈H₂₀O₄	详情	详情

Extended Information