Methyl iodide → ethyl 2-methyl-2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate
反応式
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:7][CH:8]=1.[CH3:22][Si](C)(C)[N-][Si](C)(C)C.[Li+].CI.[Cl-].[NH4+]>O1CCCC1>[CH3:22][C:9]([C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][N:7]=1)([CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]参加物
反応物 4
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 ethyl 2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate (1.18 g) in dry tetrahydrofuran (7.6 mL) was added lithium hexamethyldisilazide (1.1M tetrahydrofuran solution, 4.49 mL), and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added methyl iodide (473 μL), and the mixture was stirred at room temperature for 30 min. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the title compound (1.11 g, yield 90%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).
後処理
- stirringthe mixture was stirred at room temperature for 30 min
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
出典と根拠
- ORDレコード
- ord-6375c445a8e14d33a1085e5451017764
- 出典データセット
- uspto-grants-2012_11
- 特許番号
- US08318746B2
反応ノート
読み込み中…