硝基甲烷 → 3-Benzyloxy-trans-beta-nitrostyrene

HRID 77951

反应方程式

HRID 77951 反应方程式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([CH3:20])([O-:19])=[O:18].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:11](/[CH:12]=[CH:20]/[N+:17]([O-:19])=[O:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参与物

5

反应物 3

HCID 6375硝基甲烷HCID 743423-苄氧基苯甲醛HCID 517165乙酸铵

产物 1

HCID 53682823-Benzyloxy-trans-beta-nitrostyrene收率 89%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

反应条件

温度
100 °C

实验过程

A mixture of 3-benzyloxy-benzaldehyde (5.16 g, 24.3 mmol) described in Manufacturing Example 61-1-1, nitromethane (2.16 mL, 48.6 mmol), ammonium acetate (2.81 g, 36.5 mmol) and acetic acid (50 mL) was stirred for 6 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1-1:1) to obtain the title compound (5.50 g, 89%).

后处理

  1. temperatureThis mixture was cooled to room temperature
  2. concentrationconcentrated under a reduced pressure
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1-1:1)

来源与证据

ORD记录
ord-608c6ae546804616b361a3c77db65a46
来源数据集
uspto-grants-2014_09
专利号
US08841327B2

关联笔记

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