Tetrabutylammonium Fluoride → HCID 22926767, compound

HRID 1985417Notes

Reaction equation

HRID 1985417 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:17][CH:18]([O:24][CH:25]([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[CH:14][C:15]=1[F:16])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[F:16][C:15]1[CH:14]=[CH:13][C:12]([CH2:17][CH:18]([O:24][CH:25]([CH3:26])[CH3:27])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][C:10]=1[CH2:9][OH:8]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22927089HCID 22927089, compound

Product 1

HCID 22926767HCID 22926767, compoundYield 116.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.2 g of Ethyl 3-[3-(t-butyldimethylsilanyloxymethyl)-4-fluorophenyl]-2-isopropoxypropionate was dissolved in 15 ml of tetrahydrofuran, and 3.3 ml of 1.0M tetrabutyl ammonium fluoride in tetrahydrofuran was added. The mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography (30% ethyl acetate-hexane), to give 1.0 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-72abbb9bb5894cd1b496334e5fb7f01e
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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