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

HRID 1904969Notes

Reaction equation

HRID 1904969 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:13][OH:14])=[CH:8][CH:7]=1)[CH3:4].[O:19]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[O:19]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][O:14][CH2:13][CH:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:3][CH3:4])=[CH:11][CH:10]=1)[C:15]([F:16])([F:17])[F:18])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 10681171(RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-ol

Product 1

HCID 106695812-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-phenoxybenzyl etherYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, 132 mg of sodium hydride (60% oil dispersion) was added to 20 ml of dry DMF. A solution of 0.77 g of 2-(4-ethoxyphenyl)-3,3,3-triflouropropanol and 0.69 g of 3-phenoxybenzyl bromide in 5 ml of dry DMF was then added at room temperature, and the reaction solution was stirred at that temperature for 14 hours. Thereafter, the reaction mixture was poured into dilute HCl-ice water and extracted twice with diethyl ether. The ether layers were combined, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure, and the residue was subjected to column chromatography on silica gel [eluted with n-hexane/ethyl acetate (25:1 ) mixture] to obtain 0.61 g of the desired compound.

Workup

  1. extractionextracted twice with diethyl ether
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-7cae96bbf85c4fa9b70a467905219171
Source dataset
uspto-grants-1989_06
Patent number
US04840971

Reaction notes

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