Acetic Acid → 1,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-[(RS)-alpha-trifluoromethyl-3-phenoxybenzyloxy]prop-2-ene

HRID 483750Notes

Reaction equation

HRID 483750 reaction equation
[H-].[Na+].[F:3][C:4]([F:21])([F:20])[CH:5]([OH:19])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1.[F:22][C:23]([F:37])([F:36])[C:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[CH:29][CH:28]=1)=[CH:25]Cl.C(O)(=O)C>CN(C)C=O>[F:22][C:23]([F:36])([F:37])[C:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[CH:29][CH:28]=1)=[CH:25][O:19][CH:5]([C:4]([F:20])([F:21])[F:3])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 142705712,2,2-Trifluoro-1-(3-phenoxyphenyl)ethan-1-olHCID 540539251,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-chloroprop-2-ene

Product 1

HCID 867470201,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-[(RS)-alpha-trifluoromethyl-3-phenoxybenzyloxy]prop-2-ene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-40 °C

Procedure

Sodium hydride (0.11 g of a 50% dispersion in oil) was added to a stirred solution of α-trifluoromethyl-3-phenoxybenzyl alcohol (0.6 g, prepared according to the method of UK Patent Specification No. 1,561,575) in dry dimethylformamide. After effervescence had subsided, the resulting mixture was added dropwise to a stirred solution of EZ-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-chloroprop-2-ene (1.12 g) in dry dimethylformamide (10 cm3), the temperature of the reaction mixture being maintained at -40° C. The reaction mixture was then allowed to warm to the ambient temperature, and was stirred for 6 hours. The mixture was acidified with dilute aqueous acetic acid solution and the product extracted into diethyl ether. The combined ethereal layers were dried over anhydrous magnesium sulphate and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography on a silica gel support, eluting with dichloromethane containing 3% by volume hexane.

Workup

  1. customprepared
  2. temperatureto warm to the ambient temperature
  3. extractionthe product extracted into diethyl ether
  4. dry with materialThe combined ethereal layers were dried over anhydrous magnesium sulphate
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by column chromatography on a silica gel support
  7. washeluting with dichloromethane containing 3% by volume hexane

Sources & evidence

ORD record
ord-cbe3bedbf2ef438faf09a0a99c96fd05
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

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