甲酸钠 → alpha-Hydroxy-2-nitro-p-tolunitrile
反应方程式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].C([O-])=[O:15].[Na+]>C(O)C.O.C(Cl)Cl.CCOC(C)=O>[OH:15][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]参与物
5
实验过程
A stirred solution containing α-bromo-2-nitro-p-tolunitrile (1.228 g, 5.095 mmol) and sodium formate (0.8664 g, 12.74 mmol) in ethanol:water (4:1, 25 mL) was refluxed for 2 h. The reaction was cooled to room temperature, diluted with 20% CH2Cl2/EtOAc, washed with H2O (3×), dried (MgSO4) and concentrated. Purification by flash chromatography (1,2 and 3% MeOH/CHCl3 gradient) gave 0.695 g (77%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 4.71 (d, 2H), 5.75 (t, 1H), 7.89 (dd, J=7.9 Hz, 1H), 8.14 (d, J=7.9 Hz, 1H), 8.32 (s, 1H).
后处理
- temperaturewas refluxed for 2 h
- washwashed with H2O (3×)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customPurification by flash chromatography (1,2 and 3% MeOH/CHCl3 gradient)
来源与证据
- ORD记录
- ord-d906fe819a45423eb4f0dc114dba722f
- 来源数据集
- uspto-grants-2006_11
- 专利号
- US07132402B2
反应笔记
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