Water → 2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol

HRID 2068230Notes

Reaction equation

HRID 2068230 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:5]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].[Na+].I[CH2:28][CH2:29][O:30]C1CCCCO1.O>O1CCCC1>[Cl:1][CH2:2][CH2:3][C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:5]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:28][CH2:29][OH:30])=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 111186622H-Pyran, tetrahydro-2-(2-iodoethoxy)-2×HCID 539047244-[(1Z)-4-Chloro-1,2-diphenylbut-1-en-1-yl]phenol

Product 1

HCID 1481272-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(4-Chloro-1,2-diphenyl-but-1-enyl)phenol (0.23 g, 0.689 mmol) was dissolved in tetrahydrofuran (3 ml) under nitrogen atmosphere. Sodium hydride (0.025 g, 1.03 mmol) was added to the solution and the mixture was stirred at room temperature for an hour. 2-(2-iodo-ethoxy)-tetrahydropyran (0.3 g, 1.17 mmol) was added and the mixture was refluxed for 2 hours. Additional portions of 2-(2-iodo-ethoxy)-tetrahydro-pyran (0.5 g, 2 mmol) were added to the mixture during seven hours. After cooling and adding water, THF was evaporated and the mixture was extracted three times with ethyl acetate. The organic phase was washed with 2 N aqueous sodium hydroxide and water, dried with sodium sulphate and evaporated to dryness. The residue (which is Compound (IV) where Pr is tetrahydropyranyl) was dissolved in ethanol and acidified with 2 N aqueous hydrogen chloride solution. The mixture was stirred at room temperature over night, evaporated and extracted with dichloromethane. After washing with water the organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography with dichloromethane/methanol 9.5/0.5 as eluent. Yield 0.17 g, 59%.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. customwas evaporated
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. washThe organic phase was washed with 2 N aqueous sodium hydroxide and water
  6. dry with materialdried with sodium sulphate
  7. customevaporated to dryness
  8. dissolutionThe residue (which is Compound (IV) where Pr is tetrahydropyranyl) was dissolved in ethanol
  9. stirringThe mixture was stirred at room temperature over night
  10. customevaporated
  11. extractionextracted with dichloromethane
  12. washAfter washing with water the organic phase
  13. dry with materialwas dried (Na2SO4)
  14. customevaporated
  15. customThe residue was purified by flash chromatography with dichloromethane/methanol 9.5/0.5 as eluent

Sources & evidence

ORD record
ord-e4eae618cacf46edafbb167942865586
Source dataset
uspto-grants-2012_10
Patent number
US08293947B2

Reaction notes

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