Aluminum(III) Chloride → HCID 135856719, compound

HRID 1246555Notes

Reaction equation

HRID 1246555 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[S:14][CH:15]=[CH:16][C:12]=3[O:11][N:10]=2)=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]3[S:14][CH:15]=[CH:16][C:12]=3[O:11][N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 21915394HCID 21915394, compound

Product 1

HCID 135856719HCID 135856719, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

Treat a stirred solution of 3-(4-methoxyphenyl)thieno[2,3-d]isoxazole (9.10 g, 0.0394 mol) in 1,2-dichloroethane (100 mL) portionwise with aluminum chloride (15.74 g, 0.118 mol). The mixture is stirred at 70° C. for 1.5 hours, cool to room temperature, and decant into a mixture of concentrated hydrochloric acid (50 mL) and ice (160 g). Stir the mixture for 0.5 hour, filter through Celite, separate the phases and extract the filter cake with dichloromethane. Also use the dichloromethane extract to extract the aqueous phase. Combine the organic phases, wash twice with water, dry (Na2SO4), filter and evaporate. Purify the crude material by flash chromatography on silica gel using gradient elution with 1 to 2% methanol in dichloromethane. Concentrate the desired fractions to afford the title compound as a tan solid (7.1 g, 83% yield).

Workup

  1. temperaturecool to room temperature
  2. customdecant into a mixture of concentrated hydrochloric acid (50 mL) and ice (160 g)
  3. stirringStir the mixture for 0.5 hour
  4. filtrationfilter through Celite
  5. customseparate the phases
  6. extractionextract the filter cake with dichloromethane
  7. extractionextract
  8. extractionto extract the aqueous phase
  9. washwash twice with water
  10. dry with materialdry (Na2SO4)
  11. filtrationfilter
  12. customevaporate
  13. customPurify the crude material by flash chromatography
  14. washon silica gel using gradient elution with 1 to 2% methanol in dichloromethane
  15. concentrationConcentrate the desired fractions

Sources & evidence

ORD record
ord-800d0b99b4f3414c954f8edddff92dc4
Source dataset
uspto-grants-2006_10
Patent number
US07125903B1

Reaction notes

Loading…