Tetrabutylammonium Fluoride → HCID 58124868, compound

HRID 1971715Notes

Reaction equation

HRID 1971715 reaction equation
[C:1]([N:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][Si](C(C)(C)C)(C)C)[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCCCCCC.C(OCC)(=O)C>[C:1]([N:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58124926HCID 58124926, compound

Product 1

HCID 58124868HCID 58124868, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21899848Ethylacetate heptaneSolvent

Procedure

A solution of 2g of 16e in 20 ml of THF was treated with 11 ml of 1M tetra-n-butyl ammonium fluoride in THF at 55° C. After stirring for 1 hr the mixture was concentrated, diluted with 50 ml of 5% aq. NH4Cl and 10 ml of sat. NaCl and extracted with ethyl acetate. The organic layer was concentrated to give an oil. This was passed trough a silica pad using a gradient of heptane/ethyl acetate as eluent, to provide 1.5 g of 16f as a colorless oil, which was used without further purification in the next step.

Workup

  1. concentrationwas concentrated
  2. additiondiluted with 50 ml of 5% aq. NH4Cl and 10 ml of sat. NaCl
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customto give an oil

Sources & evidence

ORD record
ord-39afe1705bb44b2fa544f15e46ab47b5
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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