Water → HCID 17989117, compound

HRID 1443229Notes

Reaction equation

HRID 1443229 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([C:24]([F:27])([F:26])[F:25])([O:19][Si](C)(C)C)[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:28])[C:5]([C:24]([F:25])([F:27])[F:26])([OH:19])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 17989186HCID 17989186, compound

Product 1

HCID 17989117HCID 17989117, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.9 g (20.18 mmol) of contaminated ethyl-4-(4-chloro-3-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-2-(trimethylsilyloxy)-pentanoate is dissolved in 116 ml of tetrahydrofuran and mixed at room temperature with 6.37 g (20.18 mmol) of tetrabutylammonium fluoride trihydrate and stirred for one hour at room temperature. The reaction mixture is mixed with water and extracted twice with 250 ml each of diethyl ether. The combined organic extracts are washed with water and with brine. After drying on sodium sulfate, the dessicant is filtered off, the solvent is spun off, and the remaining residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 4.03 g (54.2%) of the desired compound is isolated. Other batches are implemented analogously.

Workup

  1. extractionextracted twice with 250 ml each of diethyl ether
  2. washThe combined organic extracts are washed with water and with brine
  3. customAfter drying on sodium sulfate
  4. filtrationthe dessicant is filtered off
  5. customthe remaining residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6813cdb17e74413c997cde13f3650fd3
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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