Water → HCID 17989136, compound

HRID 1443131Notes

Reaction equation

HRID 1443131 reaction equation
[F:1][C:2]1[C:3]([O:24][CH3:25])=[C:4]([C:8]([CH3:23])([CH3:22])[CH2:9][C:10]([C:18]([F:21])([F:20])[F:19])([O:13][Si](C)(C)C)[CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O.O.O.O>C1COCC1>[F:1][C:2]1[C:3]([O:24][CH3:25])=[C:4]([C:8]([CH3:23])([CH3:22])[CH2:9][C:10]([OH:13])([C:18]([F:21])([F:20])[F:19])[CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 17989217HCID 17989217, compound

Product 1

HCID 17989136HCID 17989136, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.11 g (10.75 mmol) of 4-(3-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-2-trimethylsilyloxy-pentan-1-ol is dissolved in 61 ml of THF, mixed with 3.39 g (10.746 mmol) of Bu4NF trihydrate, and stirred for one hour at room temperature. The reaction mixture is poured into water and extracted twice with diethyl ether. The organic phases are washed as usual with water and brine. After the desiccant is dried and filtered off, and after the solvent is spun in, the remaining residue is chromatographed on silica gel (mobile solvent:ethyl acetate/hexane). 2.71 g (81.4%) of the desired compound is isolated.

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe organic phases are washed as usual with water and brine
  3. customAfter the desiccant is dried
  4. filtrationfiltered off
  5. customis chromatographed on silica gel (mobile solvent:ethyl acetate/hexane)

Sources & evidence

ORD record
ord-efb6a0641992449eb08f4b134cb95da2
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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