Tetrabutylammonium Fluoride Trihydrate → HCID 17989089, compound

HRID 420630Notes

Reaction equation

HRID 420630 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C:5]([C:25]([F:28])([F:27])[F:26])([O:20][Si](C)(C)C)[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([Cl:17])[C:11]=1[O:18][CH3:19])([CH3:9])[CH3:8])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[CH2:1]([O:3][C:4](=[O:29])[C:5]([C:25]([F:26])([F:27])[F:28])([OH:20])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([Cl:17])[C:11]=1[O:18][CH3:19])([CH3:8])[CH3:9])[CH3:2]

Participants

5

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 17989303HCID 17989303, compound

Product 1

HCID 17989089HCID 17989089, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.4 g (9.67 mmol) of (rac.) 4-(3-chloro-2-methoxy-4-methylphenyl)-4-methyl-2-(trifluoromethyl)-2-trimethylsilyloxy-pentanoic acid ethyl ester is dissolved in 56 ml of tetrahydrofuran and mixed with 3.05 g (9.67 mmol) of tetrabutylammonium fluoride trihydrate and stirred for one and one-half hours at room temperature. The reaction mixture is diluted with water and extracted twice with diethyl ether. The organic phases are washed with water and with brine. After drying, the solvent is spun off, and the remaining residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 1.26 g of the desired compound is isolated.

Workup

  1. extractionextracted twice with diethyl ether
  2. washThe organic phases are washed with water and with brine
  3. customAfter drying
  4. customthe remaining residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c38d0203c7db4e8bbf16e40d2a4c66a2
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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