聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 4-Hydroxy-2-butynyl 4-Cyano-3,4-diphenylbutyrate

HRID 27826

反应方程式

HRID 27826 反应方程式
[C:1]([CH:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][C:6](Cl)=[O:7])#[N:2].[CH2:21]([OH:26])[C:22]#[C:23][CH2:24][OH:25].N1C=CC=CC=1.O>C1C=CC=CC=1.C1COCC1>[C:1]([CH:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][C:6]([O:25][CH2:24][C:23]#[C:22][CH2:21][OH:26])=[O:7])#[N:2]

参与物

7

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 1049吡啶HCID 80661,4-丁炔二醇HCID 128348424-Cyano-3,4-diphenylbutyryl chloride

产物 1

HCID 128348444-Hydroxy-2-butynyl 4-Cyano-3,4-diphenylbutyrate

试剂、催化剂与溶剂 2

HCID 241苯溶剂HCID 8028四氢呋喃溶剂

实验过程

A solution of 10.7 g (0.038 mol) of 4-cyano-3,4-diphenylbutyryl chloride in 30 ml of benzene was added over a 45 minute period to a stirred solution of 6.5 g (0.076 mol) of 2-butyn-1,4-diol and 3.4 ml of pyridine in 100 ml of THF at 0°. The reaction mixture was stirred for 24 hours at room temperature in a flask equipped with a Drierite tube. The solution was poured into 50 ml of water and the layers were separated. Two 60-ml ether extractions of the aqueous layer were combined with the THF layer, were washed twice with 100 ml of H2O, with 100 ml saturated aqueous sodium bicarbonate, and with 100 ml saturated aqueous sodium chloride and were stirred over MgSO4. The filtered solution was stripped and purified by column chromatography on silica gel (hexanes/methylene chloride) to give two fractions weighing 12.6 g (47%) having different isomer ratios as determined from the nmr spectra. The infrared and nmr spectra are in accord with the assigned structure.

后处理

  1. customequipped with a Drierite tube
  2. customthe layers were separated
  3. extractionTwo 60-ml ether extractions of the aqueous layer
  4. washwere washed twice with 100 ml of H2O, with 100 ml saturated aqueous sodium bicarbonate
  5. stirringwith 100 ml saturated aqueous sodium chloride and were stirred over MgSO4
  6. custompurified by column chromatography on silica gel (hexanes/methylene chloride)
  7. customto give two fractions

来源与证据

ORD记录
ord-cbbfd619f75b46a29115e05f3a9de54d
来源数据集
uspto-grants-1980_09
专利号
US04224052

关联笔记

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