Sodium Chloride → HCID 14516985, compound

HRID 1614443Notes

Reaction equation

HRID 1614443 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][CH:23]=1)([OH:21])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1.[H-].[Na+].[CH3:35]I.[Cl-].[Na+]>CN(C)C=O.O.C(OCC)C.CCCCCC>[F:32][C:2]([F:1])([F:31])[C:3]([O:21][CH3:35])([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH3:30])=[CH:26][CH:27]=1)[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13880758HCID 13880758, compound

Product 1

HCID 14516985HCID 14516985, compoundYield 97%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×HCID 8058HexaneSolvent

Procedure

1,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-(3-phenoxy-4-fluorobenzyloxy)propan-2-ol (0.2 g) in dry N,N-dimethyl-formamide (2 cm3) was added to a suspension of sodium hydride (0.1 g of a 50% dispersion in oil - washed free of oil with n-hexane) in N,N-dimethylformamide (2 cm3) at the ambient temperature (ca. 22° C.) under an atmosphere of nitrogen. After stirring for 20 minutes a solution of methyl iodide (0.1 g) in N,N-dimethylformamide (3 cm3) was added in one portion. After 20 minutes no starting material could be detected by gas liquid chromatographic analysis. The mixture was carefully diluted with water (30 cm3) then solid sodium chloride was added and the mixture shaken with diethyl ether. The layers were separated and the aqueous layer extracted with a further three portions of diethyl ether. The combined organic extracts were dried over anhydrous magnesium sulphate and the solvent removed by evaporation under reduced pressure. The resulting pale yellow oil was purified by chromatography on silica gel, eluting with n-hexane containing 10% by volume ethyl acetate to give 1,1,1-trifluoro-2-methoxy-2-(4-ethoxyphenyl)-3-(3-phenoxy-4-fluorobenzyloxy)propane as a colourless oil (0.2 g).

Workup

  1. additionwas added in one portion
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with a further three portions of diethyl ether
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  5. customthe solvent removed by evaporation under reduced pressure
  6. customThe resulting pale yellow oil was purified by chromatography on silica gel
  7. washeluting with n-hexane containing 10% by volume ethyl acetate

Sources & evidence

ORD record
ord-193e87c57a644d2e9cd1b4a0b9cc8b7f
Source dataset
uspto-grants-1993_03
Patent number
US05196610

Reaction notes

Loading…