Ammonium Chloride → 7-Methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-3,4-dihydronaphthalene

HRID 1926576Notes

Reaction equation

HRID 1926576 reaction equation
I[CH:2]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:20][CH:19]=2)[C:9]2[C:4](=[CH:5][C:6]([O:31][CH3:32])=[CH:7][CH:8]=2)[CH2:3]1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:32][O:31][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]([C:18]3[CH:19]=[CH:20][C:21]([O:24][C:25](=[O:30])[C:26]([CH3:28])([CH3:27])[CH3:29])=[CH:22][CH:23]=3)[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:2]=[CH:3]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 251119892-Iodo-7-methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 575434947-Methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-3,4-dihydronaphthaleneYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-iodo-7-methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-1,2,3,4-tetrahydronaphthalene (5, 39.4 mg, 0.0729 mmol) was dissolved in toluene (1.5 mL), and 1,8-diaza-bicyclo[5.4.0]undecene-7 (DBU, 0.035 mL, 0.234 mmol) was added, with heating and stirring at 80° c. for 15 min. After standing to cool, a saturated ammonium chloride aqueous solution (10 mL) was added under ice cooling, vigorously stirred, and next, extraction was carried out adding diethyl ether (10 mL). Extractions were further carried out two times with diethyl ether (10 mL), the organic phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated. The residue was purified by thin layer chromatography (benzene:hexane=10:1), and the subject compound (6, 22.7 mg) was obtained as a colorless oily substance (yield=75%).

Workup

  1. temperaturewith heating
  2. temperatureto cool
  3. stirringvigorously stirred
  4. extractionnext, extraction
  5. additionwas carried out adding diethyl ether (10 mL)
  6. extractionExtractions
  7. washwashed with a saturated sodium chloride aqueous solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by thin layer chromatography (benzene:hexane=10:1)
  11. customthe subject compound (6, 22.7 mg) was obtained as a colorless oily substance (yield=75%)

Sources & evidence

ORD record
ord-5a579ab8e05d4f66a41c8b599a3baa7a
Source dataset
uspto-grants-2012_05
Patent number
US08183235B2

Reaction notes

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