Ethanol → HCID 21281080, compound

HRID 414504Notes

Reaction equation

HRID 414504 reaction equation
[F:1][CH:2]([F:26])[C:3]([CH3:25])([CH3:24])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)C(=O)C)[CH:8]=1.[OH-].[K+].C(O)C.C(OCC)(=O)C>O>[F:26][CH:2]([F:1])[C:3]([CH3:24])([CH3:25])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([NH:14][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 212810891,1-Difluoro-2,2-dimethyl-3-[3-(N-phenyl-N-acetylamino)-4-fluorobenzyloxy]propane

Product 1

HCID 21281080HCID 21281080, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,1-Difluoro-2,2-dimethyl-3-[3-(N-phenyl-N-acetylamino)-4fluorobenzyloxy]propane (0.5 g) was suspended in a 1 molar solution of potassium hydroxide in water containing 20% by volume ethanol and the mixture was heated at the reflux temperature for 8 hours. After standing overnight at the ambient temperature, the mixture was shaken several times with ethyl acetate and the combined organic extracts washed with water and brine, and dried over anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure gave a brown oil which was purified by column chromatography on a silica gel supoort, eluting with petroleum ether (boiling range 40°-60° C.) containing 10% by volume ethyl acetate, to give the title compound (0.23 g) as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated at the reflux temperature for 8 hours
  2. washthe combined organic extracts washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customEvaporation of the solvent under reduced pressure
  5. customgave a brown oil which
  6. customwas purified by column chromatography on a silica gel supoort
  7. washeluting with petroleum ether (boiling range 40°-60° C.)
  8. additioncontaining 10% by volume ethyl acetate

Sources & evidence

ORD record
ord-a97baa1ff93c429eb52f47454fbbfa89
Source dataset
uspto-grants-1988_12
Patent number
US04792563

Reaction notes

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