Pyridine → HCID 19753523, compound

HRID 1614442Notes

Reaction equation

HRID 1614442 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3](C1C=CC(OCC)=CC=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.N1C=CC=CC=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>O>[F:32][C:2]([F:1])([F:31])[CH:3]([O:21][C:39](=[O:41])[CH3:40])[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:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13880758HCID 13880758, compound

Product 1

HCID 19753523HCID 19753523, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-(3-phenoxy-4-fluorobenzyloxy)propan-2-ol (0.3 g), pyridine (1 cm3), acetic anhydride (10 cm3) and a catalytic amount of 4-N,N-dimethylaminopyridine (ca. 0.015 g) were mixed at the ambient temperature (ca. 22° C.), then heated at the reflux temperature for 6 hours. The mixture was allowed to stand overnight at the ambient temperature, and was then heated at reflux for a further 6 hours. Analysis by gas liquid chromatography showed 94% conversion to the product. Water was added and the product was extracted into diethyl ether (5×50 cm3). The combined ether layers were dried over anhydrous sodium sulphate and concentrated by evaporation under reduced pressure. The residual oil was purified by column chromatography on a silica gel support, eluted with n-hexane containing 12% by volume ethyl acetate, to give 1,1,1-trifluoro-2-acetoxy-3-(3-phenoxy-4-fluorobenzyloxy)propane (0.29 g) as a viscous oil.

Workup

  1. temperatureheated at the reflux temperature for 6 hours
  2. temperaturewas then heated
  3. temperatureat reflux for a further 6 hours
  4. extractionthe product was extracted into diethyl ether (5×50 cm3)
  5. dry with materialThe combined ether layers were dried over anhydrous sodium sulphate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residual oil was purified by column chromatography on a silica gel support
  8. washeluted with n-hexane containing 12% by volume ethyl acetate

Sources & evidence

ORD record
ord-2c43e95957e84c249853a1613b140d49
Source dataset
uspto-grants-1993_03
Patent number
US05196610

Reaction notes

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