Glycol monoethyl ether → 3-(3-Methoxyphenyl)thieno[2,3-d]isoxazole

HRID 1246550

Reaction equation

HRID 1246550 reaction equation
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

Participants

6

Reactant 3

HCID 8076Glycol monoethyl etherHCID 14797Potassium HydroxideHCID 72727313(3-Bromothien-2-yl) (3-methoxyphenyl)methanone oxime

Product 1

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

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 8058HexaneSolvent

Procedure

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 (100 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 reaction for an additional one hour. 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.

Workup

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

Sources & evidence

ORD record
ord-0cbaf1b30fa141aa8b11baa26f977eee
Source dataset
uspto-grants-2006_10
Patent number
US07125903B1

Linked notes

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