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

HRID 217316Notes

Reaction equation

HRID 217316 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 75.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

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), then 1,8-diazabicyclo[5.4.0]undecene-7 (DBU, 0.035 mL, 0.234 mmol) was added thereto, and the mixture was stirred for 15 minutes while heating at 80° C. After allowing cooling, a saturated aqueous ammonium chloride solution (10 mL) was added under cooling by ice, and then the mixture was intensively stirred and extracted by adding ether (10 mL). The reaction mixture was further extracted two times using ether (10 mL), and then an organic layer was collected and rinsed with a saturated aqueous sodium chloride solution, followed by drying with anhydrous magnesium sulfate and concentration thereof. The residue was purified by thin layer chromatography (benzene/hexane=10/1) to obtain the title compound (6, 22.7 mg) as a colorless oily substance (yield 75%).

Workup

  1. temperatureAfter allowing cooling
  2. temperatureunder cooling by ice
  3. stirringthe mixture was intensively stirred
  4. extractionextracted
  5. additionby adding ether (10 mL)
  6. extractionThe reaction mixture was further extracted two times
  7. customan organic layer was collected
  8. washrinsed with a saturated aqueous sodium chloride solution
  9. dry with materialby drying with anhydrous magnesium sulfate and concentration
  10. customThe residue was purified by thin layer chromatography (benzene/hexane=10/1)

Sources & evidence

ORD record
ord-0ce2bea118f84347914643fac2e0f60c
Source dataset
uspto-grants-2012_06
Patent number
US08193394B2

Reaction notes

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