反応式
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].[CH2:21](I)[CH3:22].[CH2:24]1COC[CH2:25]1>CN(C=O)C>[CH2:24]([C:15]([C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:18])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)([CH2:21][CH3:22])[C:16]#[N:17])[CH3:25]参加物
6
実験手順
To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (2.0 g, 8.23 mmol) in DMF (40 mL) was cooled to 0° C. and sodium hydride (60 wt %, 1.2 g, 32.9 mmol) added portion wise. The mixture was stirred for 10 min and ethyl iodide (0.74 mL, 9.05 mmol) in THF (10 mL) was added. The mixture was stirred at room temperature for 12 h. The reaction mixture was quenched with water and diluted with ethyl acetate. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (950 mg, 38%) as a brown solid: ESI MS m/z 300 [C18H26BNO2+H]+.
後処理
- stirringThe mixture was stirred at room temperature for 12 h
- customThe reaction mixture was quenched with water
- additiondiluted with ethyl acetate
- customThe layers were separated
- dry with materialthe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customthe residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane)
出典と根拠
- ORDレコード
- ord-23bd53f8e0c444068da1b35f3745bbb6
- 出典データセット
- uspto-grants-2015_02
- 特許番号
- US08962648B2
関連ノート
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