乙酐 → (Z)-3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene

HRID 369669笔记

反应方程式

HRID 369669 反应方程式
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6](Cl)(Cl)[C:7]([F:10])([F:9])[F:8].[CH2:13]([C:15]1[CH:30]=[C:29]([O:31][CH2:32][CH:33]=[C:34]([Cl:36])[Cl:35])[CH:28]=[C:27]([CH2:37][CH3:38])[C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH:25]=O)[CH3:14].C(OC(=O)C)(=O)C>[Zn].CN(C)C=O>[CH2:13]([C:15]1[CH:30]=[C:29]([O:31][CH2:32][CH:33]=[C:34]([Cl:35])[Cl:36])[CH:28]=[C:27]([CH2:37][CH3:38])[C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24]/[CH:25]=[C:6](\[Cl:5])/[C:7]([F:10])([F:9])[F:8])[CH3:14]

参与物

7

反应物 4

HCID 7918乙酐HCID 96351,1,1-三氯三氟乙烷HCID 6451240三氯化铝HCID 537387765-(2,6-Diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde

产物 1

HCID 86755968(Z)-3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene收率 192.5%

试剂、催化剂与溶剂 2

HCID 23994Zinc催化剂HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

To a mixture of 0.12 g of aluminum chloride and 50 ml of N,N-dimethylformamide was added 3.04 g of 1,1,1-trichlorotrifluoroethane. After stirring at room temperature for 1 hour, 1.21 g of 5-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde was added, and the reaction mixture was further stirred at room temperature for 4 hours, to which 1.38 g of acetic anhydride was added. After stirring at room temperature for 1 hour, 0.88 g of zinc dust was added, and the reaction mixture was stirred at room temperature for 12 hours and filtered. The filtrate was poured into 50 ml of diluted hydrochloric acid and extracted twice with 100 ml of diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 2.91 g of (Z)-3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene (yield, 72%), nD26.0 1.4958.

后处理

  1. additionwas added
  2. stirringAfter stirring at room temperature for 1 hour
  3. stirringthe reaction mixture was stirred at room temperature for 12 hours
  4. filtrationfiltered
  5. additionThe filtrate was poured into 50 ml of diluted hydrochloric acid
  6. extractionextracted twice with 100 ml of diethyl ether
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customto give a crude product

来源与证据

ORD记录
ord-e8a7db0a2be54d9580a7dbbfe22b336d
来源数据集
uspto-grants-2000_10
专利号
US06140274

反应笔记

加载中…