Dichloromethane → 3-Thieno[2,3-d]isoxazol-3-yl-phenol

HRID 8643Notes

Reaction equation

HRID 8643 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:13]3[S:14][CH:15]=[CH:16][C:12]=3[O:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.Cl.N1C=CC=CC=1.C(OCC)(=O)C.ClCCl>O>[O:11]1[C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:9]([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)=[N:10]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 10176127Pyridinium chlorideHCID 140972413-(3-Methoxyphenyl)thieno[2,3-d]isoxazole

Product 1

HCID 140972423-Thieno[2,3-d]isoxazol-3-yl-phenolYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

Combine and stir under nitrogen at 140° C. a mixture of 3-(3-methoxyphenyl)thieno[2,3-d]isoxazole (8 g, 0.035 mol) and pyridine hydrochloride (80 g, 0.69 mol) for nine hours. TLC (ethyl acetate: dichloromethane) shows the reaction is complete. Cool the reaction mixture to room temperature, and pour into water. Extract the organics into ethyl acetate:ether (50:50), and wash once with HCl (3N), three times with water, dry (MgSO4) and evaporate to yield an oil. Purify the oil by column (silica) chromatography, eluting with 5% ethyl acetate in dichloromethane, to yield a solid. Recrystallize this solid (ether:hexane) to obtain the title compound as an orange/tan solid (3 g, 40% yield), m.p. 114–116° C.

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. extractionExtract the organics into ethyl acetate:ether (50:50)
  3. washwash once with HCl (3N), three times with water
  4. dry with materialdry (MgSO4)
  5. customevaporate
  6. customto yield an oil
  7. customPurify the oil by column (silica) chromatography
  8. washeluting with 5% ethyl acetate in dichloromethane
  9. customto yield a solid
  10. customRecrystallize this solid (ether:hexane)

Sources & evidence

ORD record
ord-130240c6a61a4ba39e2fdcb60136612f
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Reaction notes

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