p-Toluenesulfonic acid → HCID 21939739, compound

HRID 1242908Notes

Reaction equation

HRID 1242908 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.C(Cl)(Cl)Cl.[CH:16]1[C:25]2[CH2:24][CH2:23][CH:22]=[CH:21][C:20]=2[CH:19]=[CH:18][C:17]=1[NH:26][C:27](=[O:29])[CH3:28].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:27]([NH:26][C:17]1[CH:16]=[C:25]2[C:20](=[CH:19][CH:18]=1)[CH2:21][C:22](=[O:9])[CH2:23][CH2:24]2)(=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6212ChloroformHCID 70297m-Chloroperbenzoic acidHCID 21939847HCID 21939847, compound

Product 1

HCID 21939739HCID 21939739, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

m-Chloroperbenzoic acid (5.13 g, 20.8 mmol) was added to a chloroform solution (80 ml) of N-(7,8-dihydro-2-naphthalenyl)acetamide (3.00 g, 16.0 mmol) obtained in 1) under ice-cooling, which was stirred at room temperature for 2 hours. Ethyl acetate was added to the reaction mixture, which was washed with saturated sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by alumina B column chromatography (development solvent; hexane:ethyl acetate=1:1). 1N Sodium hydroxide solution (10.7 ml) was added to a methanol solution (100 ml) of the obtained oily substance (3.20 g, 8.89 mmol) under ice-cooling, which was stirred at room temperature for 30 minutes. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by alumina B column chromatography (development solvent; ethyl acetate: methanol=10:1). p-Toluenesulfonic acid (50 mg, 0.262 mmol) and toluene (26 ml) were added to the obtained diol (596 mg, 2.62 mmol), which was stirred at 120° C. for 3 hours. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:3), and powdered with diisopropyl ether, to give the titled compound (231 mg).

Workup

  1. customobtained in 1) under ice-
  2. temperaturecooling
  3. washwas washed with saturated sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe resulting oily substance was purified by alumina B column chromatography (development solvent; hexane:ethyl acetate=1:1)
  7. addition1N Sodium hydroxide solution (10.7 ml) was added to a methanol solution (100 ml) of the obtained oily substance (3.20 g, 8.89 mmol) under ice-
  8. temperaturecooling
  9. stirringwhich was stirred at room temperature for 30 minutes
  10. distillationThe solvent was distilled out under reduced pressure
  11. additionEthyl acetate was added to the residue, which
  12. washwas washed with saturated aqueous sodium chloride solution
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationthe solvent was distilled out under reduced pressure
  15. customThe resulting oily substance was purified by alumina B column chromatography (development solvent; ethyl acetate: methanol=10:1)
  16. stirringwas stirred at 120° C. for 3 hours
  17. distillationThe solvent was distilled out under reduced pressure
  18. additionEthyl acetate was added to the residue, which
  19. washwas washed with saturated aqueous sodium chloride solution
  20. dry with materialdried over anhydrous sodium sulfate
  21. distillationthe solvent was distilled out under reduced pressure
  22. customThe resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-11cf5511037a40509630b087d1acd556
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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