Ethyl 3-(trimethylsilyl)propynoate → Methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4-methoxybenzoate
反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:31][Si:32]([CH3:41])([CH3:40])[C:33]#[C:34][C:35](OCC)=[O:36]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[C:12]([O:14][CH3:15])=[O:13])[C:35](=[O:36])[C:34]#[C:33][Si:32]([CH3:41])([CH3:40])[CH3:31])=[CH:4][CH:3]=1参加物
5
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
To a solution of methyl 3-[(6-chloropyridazin-3-yl)methyl]-4-methoxybenzoate (10.03 g, 34.2 mmol) in THF (400 mL) was added LHMDS (100 mL, 1M solution in THF) and ethyl 3-(trimethylsilyl)propynoate (6.66 mL, 35.5 mmol) at −78° C. The reaction was warmed to 0° C. and stirred for 0.5 hr until the reaction was complete by LCMS analysis. The reaction was quenched with aqueous NH4Cl and extracted with ethyl acetate. The combined organic layers were washed with 0.5 N HCl, brine, dried over MgSO4, and condensed in vacuo to yield an oil. The crude material was purified via silica gel chromatography (CH2Cl2) to yield the title compound.
後処理
- customThe reaction was quenched with aqueous NH4Cl
- extractionextracted with ethyl acetate
- washThe combined organic layers were washed with 0.5 N HCl, brine
- dry with materialdried over MgSO4, and condensed in vacuo
- customto yield an oil
- customThe crude material was purified via silica gel chromatography (CH2Cl2)
出典と根拠
- ORDレコード
- ord-0da6cc5dba5a4bcbbc4969e7a8ac72c1
- 出典データセット
- uspto-grants-2009_01
- 特許番号
- US07482345B2
反応ノート
読み込み中…