丙二腈 → 二氢-2H-吡喃-4,4(3H)-二甲腈

HRID 12506

反应方程式

HRID 12506 反应方程式
[C:1](#[N:5])[CH2:2][C:3]#[N:4].Br[CH2:7][CH2:8][O:9][CH2:10][CH2:11]Br.CC([O-])(C)C.[K+]>CS(C)=O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C(Cl)Cl>[O:9]1[CH2:10][CH2:11][C:2]([C:1]#[N:5])([C:3]#[N:4])[CH2:7][CH2:8]1

参与物

7

反应物 3

HCID 8010丙二腈HCID 215212,2'-二溴二乙醚HCID 23665647叔丁醇钾

产物 1

HCID 14537194二氢-2H-吡喃-4,4(3H)-二甲腈收率 24%

试剂、催化剂与溶剂 3

HCID 74236四丁基溴化铵催化剂HCID 679二甲基亚砜溶剂HCID 6344二氯甲烷溶剂

实验过程

Malononitrile (5.0 g) was dissolved in DMSO (5 mL). Subsequently, bis(2-bromoethyl)ether (9.49 mL) and TBAB (1.22 g) were added, followed by portionwise addition of KOtBu (8.49 g). The mixture was stirred for 4 h. at room temperature, taken up in DCM and extracted 3 times with 5% aqueous NaHCO3. The organic phase was dried over Na2SO4 and evaporated under reduced pressure. The crude material was purified by flash chromatography eluting with PA:Et2O 65:35 (Rf=0.24, visualized with KMnO4) to give 2.49 g (24%) of a solid. 1H NMR (400 MHz, CDCl3) δ 2.24 (t, 4H), 3.87 (t, 4H).

后处理

  1. extractionextracted 3 times with 5% aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated under reduced pressure
  4. customThe crude material was purified by flash chromatography
  5. washeluting with PA

来源与证据

ORD记录
ord-4052a6dbde5847328dbec77949a0b930
来源数据集
uspto-grants-2010_06
专利号
US07728018B2

关联笔记

加载中…