乙二醇乙醚 → 3-(3-Methoxyphenyl)thieno[2,3-d]isoxazole

HRID 8642

反应方程式

HRID 8642 反应方程式
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)=[N:8][OH:9].[OH-].[K+].C(OCCO)C>[Cu](Cl)Cl.CCCCCC>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([C:7]2[C:3]3[S:4][CH:5]=[CH:6][C:2]=3[O:9][N:8]=2)[CH:15]=[CH:14][CH:13]=1

参与物

6

反应物 3

HCID 8076乙二醇乙醚HCID 14797氢氧化钾HCID 72727313(3-Bromothien-2-yl) (3-methoxyphenyl)methanone oxime

产物 1

HCID 140972413-(3-Methoxyphenyl)thieno[2,3-d]isoxazole收率 68%

试剂、催化剂与溶剂 2

HCID 24014氯化铜催化剂HCID 8058正己烷溶剂

实验过程

Reflux a mixture of (3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone oxime (10 g, 0.032 mol), KOH (3.6 g, 0.064 mol dissolved in 10 mL water) and 2-ethoxyethanol (40 mL) under nitrogen for one hour at 105–110° C. Add copper chloride (0.16 g, 0.0016 mol) whereupon the reaction mixture becomes dark brown in color. Heat the reacton for an additional four hours. TLC shows that the reaction is complete. Add water and extract the organics into ether. Wash the ether phase with water, dry (MgSO4), filter and concentrate to yield an oil. Purify the oil by column (alumina) chromatography, and elute with 15% ether in hexane to obtain white crystals. Recrystallize the crystals from ether:hexane to yield the title compound (5 g, 68% Yield), m.p. 51–52° C.

后处理

  1. temperatureReflux
  2. temperatureHeat the reacton for an additional four hours
  3. extractionAdd water and extract the organics into ether
  4. washWash the ether phase with water
  5. dry with materialdry (MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto yield an oil
  9. customPurify the oil by column (alumina) chromatography
  10. washelute with 15% ether in hexane
  11. customto obtain white crystals
  12. customRecrystallize the crystals from ether

来源与证据

ORD记录
ord-4403c65bc86f4873a07629c666db5d15
来源数据集
uspto-grants-2006_08
专利号
US07091199B1

关联笔记

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