Tetrabutylammonium Fluoride → HCID 22568877, compound

HRID 2185315Notes

Reaction equation

HRID 2185315 reaction equation
[CH2:1]([O:3][C:4]1([C:7]2[CH:23]=[CH:22][C:10]([O:11][Si](C(C)C)(C(C)C)C(C)C)=[CH:9][C:8]=2[CH:24]([CH3:26])[CH3:25])[CH2:6][CH2:5]1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:3][C:4]1([C:7]2[CH:23]=[CH:22][C:10]([OH:11])=[CH:9][C:8]=2[CH:24]([CH3:25])[CH3:26])[CH2:6][CH2:5]1)[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22568798HCID 22568798, compound2×

Product 1

HCID 22568877HCID 22568877, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of [4-(1-ethoxycyclopropyl)-3-isopropyl-phenoxy]-triisopropyl-silane (Intermediate 99, 360.0 mg, 0.96mmol) in 3 mL THF at 0° C. was added tetrabutylammonium fluoride (625.0 mg, 2.39 mmols, 2.4 mL of a 1 M solution in THF). The solution was stirred at 0° C. for 30 minutes and then quenched by the addition of H2O. The mixture was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound (180 mg, 86%) was isolated from the residue by column chromatography (4-10% EtOAc-hexanes) as a colorless solid.

Workup

  1. customquenched by the addition of H2O
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  4. dry with materialbefore being dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14fcc194d6cc4d44bca36017e98817e2
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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