Dimethylformamide → HCID 14516985, compound

HRID 483724Notes

Reaction equation

HRID 483724 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]N(C)C=O>>[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

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 13880758HCID 13880758, compound

Product 1

HCID 14516985HCID 14516985, compound

Procedure

1,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-(3-phenoxy-4-fluorobenzyloxy)propan-2-ol (0.2 g) in dry N,N-dimethylformamide (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. washwashed free of oil with n -hexane) in N,N-dimethylformamide (2 cm3) at the ambient temperature (ca. 22° C.) under an atmosphere of nitrogen
  2. additionwas added in one portion
  3. waitAfter 20 minutes no starting material could be detected by gas liquid chromatographic analysis
  4. additionThe mixture was carefully diluted with water (30 cm3)
  5. additionsolid sodium chloride was added
  6. stirringthe mixture shaken with diethyl ether
  7. customThe layers were separated
  8. extractionthe aqueous layer extracted with a further three portions of diethyl ether
  9. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  10. customthe solvent removed by evaporation under reduced pressure
  11. customThe resulting pale yellow oil was purified by chromatography on silica gel
  12. washeluting with n-hexane containing 10% by volume ethyl acetate

Sources & evidence

ORD record
ord-05517b65aba847519a7624897103d330
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

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