咪唑 → 3-(t-Butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile

HRID 11459

反应方程式

HRID 11459 反应方程式
N1C=CN=C1.CN(C)C=O.[OH:11][CH:12]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:13][C:14]#[N:15].[C:22]([Si:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)Cl)([CH3:25])([CH3:24])[CH3:23]>CCOCC.C(OCC)(=O)C>[O:11]([CH:12]([C:16]1[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=1)[CH2:13][C:14]#[N:15])[Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参与物

7

反应物 4

HCID 795咪唑HCID 6228N,N-二甲基甲酰胺HCID 94078叔丁基二苯基氯硅烷HCID 219739393-Hydroxy-3-(pyridin-4-yl)propanenitrile

产物 1

HCID 219742193-(t-Butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile收率 98.9%

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂HCID 8857乙酸乙酯溶剂

实验过程

Next, imidazole (4.60 g, 67.5 mmol) and N,N-dimethylformamide (30 ml) were added to the obtained 3-hydroxy-3-(4-pyridyl)propionitrile (1.00 g, 6.75 mmol), and the mixture was stirred at room temperature. t-Butyldiphenylchlorosilane (2.23 g, 8.10 mmol) was added to the mixture, and the whole was stirred for one day and further stirred at an external temperature of 50° C. for three hours. Ethyl acetate (50 ml) and ether (50 ml) were added to the reaction mixture, the whole was washed with water (20 ml) three times and saturated brine (30 ml) successively, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 2.58 g (98.9%) of 3-(t-butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile as a colorless oily matter.

后处理

  1. stirringthe whole was stirred for one day
  2. stirringfurther stirred at an external temperature of 50° C. for three hours
  3. washthe whole was washed with water (20 ml) three times and saturated brine (30 ml) successively
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

来源与证据

ORD记录
ord-5796659c7f674d9aaacb6e64badd6d98
来源数据集
uspto-grants-2006_08
专利号
US07098226B2

关联笔记

加载中…