Tetrabutylammonium Fluoride → HCID 22062708, compound

HRID 2353004Notes

Reaction equation

HRID 2353004 reaction equation
C([Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24])(C)C)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:9]([OH:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59379078HCID 59379078, compound

Product 1

HCID 22062708HCID 22062708, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 11.0 g (31 mmol) of 25 was added 124 mL of a 1 M solution of TBAF in THF and the reaction was stirred for 16 h at room temperature. The reaction mixture was then quenched with saturated solution of aq. NH4Cl and THF was evaporated under reduced pressure. The aq. solution was then diluted with 200 mL of water and the target product was extracted with Et2O (3×), the combined organic layers were then washed with brine (1×), dried over MgSO4 and the solvent was removed under reduced pressure. The crude was then purified by combiflash using hexane/ethyl acetate as eluent to furnish 5.7 g of target product 26 in 77% yield as colorless oil.

Workup

  1. customThe reaction mixture was then quenched with saturated solution of aq. NH4Cl and THF
  2. customwas evaporated under reduced pressure
  3. additionThe aq. solution was then diluted with 200 mL of water
  4. extractionthe target product was extracted with Et2O (3×)
  5. washthe combined organic layers were then washed with brine (1×)
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed under reduced pressure
  8. customThe crude was then purified by combiflash

Sources & evidence

ORD record
ord-e6bee84150cd4c508a09deecc2835c27
Source dataset
uspto-grants-2010_07
Patent number
US07749983B2

Reaction notes

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