Toluene → HCID 58107492、化合物
反応式
COC(=O)[CH2:4][CH2:5][NH:6][CH3:7].C1C2[C:12](=CC=CC=2)[CH2:11][C:10]1=[O:18].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH3:7][N:6]1[C:10](=[O:18])[CH2:11][CH2:12][C:25]2[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:4][C:5]1=2参加物
実験手順
3-Methylamino-propionic acid methyl ester (1.5 g, 13.64 mmol) is added to a solution of 2-indanone (1.7 g, 12.86 mmol) in toluene (20 mL) and the reaction is brought to reflux for 2.5 hours. Toluene is removed in vacuo and the residue is dissolved in ethylene glycol (17 mL) and the resulting solution is heated to reflux for 8 hours. The reaction is allowed to cool to ambient temperature, is poured over water and extracted with dichloromethane. The organic phase is dried over magnesium sulfate and concentrated in vacuo to afford the crude title compound as a brown oil. The crude product is purified by silica gel chromatography (gradient of ethyl acetate in hexanes 10-100%) affording 720 mg (28% yield) of the title compound. 1H NMR (CDCl3) δ2.70-2.80 (m, 4H), 3.23 (s, 3H), 3.5 (s, 2H), 7.07-7.15 (m, 2H), 7.24-7.33 (m, 1H), 7.38 (d, 1H, J=7.07). MS (m/z): 199.2 (M+1).
後処理
- temperatureto reflux for 2.5 hours
- customToluene is removed in vacuo
- dissolutionthe residue is dissolved in ethylene glycol (17 mL)
- temperaturethe resulting solution is heated
- temperatureto reflux for 8 hours
- additionis poured over water
- extractionextracted with dichloromethane
- dry with materialThe organic phase is dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customto afford the crude title compound as a brown oil
- customThe crude product is purified by silica gel chromatography (gradient of ethyl acetate in hexanes 10-100%)
出典と根拠
- ORDレコード
- ord-a4acbebf32894f3d8f6cade176ebcdeb
- 出典データセット
- uspto-grants-2012_07
- 特許番号
- US08222424B2
反応ノート
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