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

HRID 8642

Reaction equation

HRID 8642 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 (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.

Workup

  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

Sources & evidence

ORD record
ord-4403c65bc86f4873a07629c666db5d15
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Linked notes

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