Water → 2-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-phenoxybenzyl ether

HRID 1614445Notes

Reaction equation

HRID 1614445 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.[F:13][C:14]([F:43])([F:42])[C:15](Cl)([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH3:40])=[CH:34][CH:33]=1)[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1.C([SnH](CCCC)CCCC)CCC.O>C1(C)C=CC=CC=1>[F:13][C:14]([F:42])([F:43])[CH:15]([C:32]1[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH3:40])=[CH:36][CH:37]=1)[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 145169861,1,1-Trifluoro-2-chloro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propane

Product 1

HCID 106695812-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-phenoxybenzyl etherYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A few crystals of α,α-azoisobutyronitrile (AIBN) were added to a solution of 1,1,1-trifluoro-2-chloro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propane (0.36 g) in toluene (15 cm3), and the mixture was cooled in an ice bath whilst tri-n-butyl tin hydride (0.25 cm3) was added. The reaction mixture was heated at the reflux temperature for 1.5 hours under an atmosphere of nitrogen. Analysis by gas liquid chromatography at this time showed no trace of the starting chloro compound. The mixture was cooled, poured I into water (50 cm3), and extracted with diethyl ether (4×30 cm3). The combined organic layers were dried over anhydrous sodium sulphate and the residual oil after evaporation of the solvent under reduced pressure was purified by column chromatography on a silica gel support, eluting with n-hexane containing 6% by volume diethyl ether, to give 1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)-propane (0.3 g) as an oil.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated at the reflux temperature for 1.5 hours under an atmosphere of nitrogen
  3. temperatureThe mixture was cooled
  4. extractionextracted with diethyl ether (4×30 cm3)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  6. customthe residual oil after evaporation of the solvent under reduced pressure
  7. customwas purified by column chromatography on a silica gel support
  8. washeluting with n-hexane containing 6% by volume diethyl ether

Sources & evidence

ORD record
ord-1c69224a0c674af7b7e6d4994595723f
Source dataset
uspto-grants-1993_03
Patent number
US05196610

Reaction notes

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