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

HRID 568515Notes

Reaction equation

HRID 568515 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>>[OH: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

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 140972413-(3-Methoxyphenyl)thieno[2,3-d]isoxazole

Product 1

HCID 140972423-Thieno[2,3-d]isoxazol-3-yl-phenolYield 39.9%

Procedure

Eight grams of 3-(3-methoxyphenyl)thieno[2,3-d)isoxazole was stirred with 80 g of pyridine hydrochloride for nine hours under nitrogen at 140° C. The reaction mixture was then allowed to cool and quenched with water. The organics were extracted into ether/ethyl acetate (1:1), which was then washed once with 3N hydrochloric acid and three times with water an dried over anhydrous magnesium sulfate. Evaporation of the solvents left 4 g of an oil, which was passed through a silica gel column packed in hexane. Elution of the column with 5% ethyl acetate/dichloromethane and recrystallization of the resultant solid from ether/hexane gave 3 g of a solid, m.p. 114°-116° C.

Workup

  1. temperatureto cool
  2. customquenched with water
  3. extractionThe organics were extracted into ether/ethyl acetate (1:1), which
  4. washwas then washed once with 3N hydrochloric acid and three times with water
  5. dry with materialan dried over anhydrous magnesium sulfate
  6. customEvaporation of the solvents
  7. waitleft 4 g of an oil, which
  8. washElution of the column
  9. customwith 5% ethyl acetate/dichloromethane and recrystallization of the resultant solid from ether/hexane

Sources & evidence

ORD record
ord-233821ebcf8a418180a0ddc30c345102
Source dataset
uspto-grants-1988_03
Patent number
US04728651

Reaction notes

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