Sodium hydride → HCID 14053992, compound

HRID 1904970Notes

Reaction equation

HRID 1904970 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].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][C:21]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:14][CH2:13][CH:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:3][CH3:4])=[CH:11][CH:10]=2)[C:15]([F:16])([F:17])[F:18])=[CH:22][C:21]=1[O:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10681171(RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-olHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzene

Product 1

HCID 14053992HCID 14053992, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, 113 mg of sodium hydride (60% oil dispersion) was added to 20 ml of dry DMF. A solution of 0.60 g of 2-(4-ethoxyphenyl)-3,3,3-trifluoropropanol and 0.65 g of 4-fluoro-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 15 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 0.64 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-6aa3e74e16ea4852bf57ea81a5f603e9
Source dataset
uspto-grants-1989_06
Patent number
US04840971

Reaction notes

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