p-Toluenesulfonic acid → HCID 19047571, compound

HRID 1451336Notes

Reaction equation

HRID 1451336 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2(O)[C:14]3[O:13][N:12]=[C:11]([CH3:15])[C:10]=3[CH2:9][CH2:8][CH2:7]2)=[CH:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:14]3[O:13][N:12]=[C:11]([CH3:15])[C:10]=3[CH2:9][CH2:8][CH:7]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19974084HCID 19974084, compound

Product 1

HCID 19047571HCID 19047571, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 7.6 g (0.034 mol) of 7-(3-furyl)-3-methyl-4,5,6,7-tetrahydro-benzisoxazol-7-ol in 300 ml of toluene was added 100 mg of p-toluenesulfonic acid and the mixture was placed on a Rotovap, and the solvent was distilled in vacuo (80° C.) until an oil residue was obtained. Toluene (200 ml) was added to the above residue, the mixture was placed on Rotovap, and the solvent was distilled in vacuo to complete the reaction. The oil was chromatographed (silica, 1:1 hexane/methylene chloride) to afford 3.36 g (95%) of 7-(3-furyl)-3-methyl-4,5-dihydrobenzisoxazole, (Formula III: R2 =H; ##STR8## R4 =3-furanyl) as a clear oil.

Workup

  1. distillationthe solvent was distilled in vacuo (80° C.) until an oil residue
  2. customwas obtained
  3. distillationthe solvent was distilled in vacuo
  4. customthe reaction
  5. customThe oil was chromatographed (silica, 1:1 hexane/methylene chloride)

Sources & evidence

ORD record
ord-6c94e904714e46d2916919a67d8fc085
Source dataset
uspto-grants-1997_02
Patent number
US05604224

Reaction notes

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