Tetrahydrofuran → HCID 54223603, compound

HRID 1885638Notes

Reaction equation

HRID 1885638 reaction equation
[SiH3]O[SiH3].O.O.O.[F-:7].C([N+]([CH2:21][CH2:22][CH2:23][CH3:24])(CCCC)CCCC)CCC.[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[F:7][C:21](=[CH:22][CH2:23][CH:24]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:21][CH:22]=[CH:23][CH2:24][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:29][CH2:28][CH2:27][CH2:26][OH:25]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 123318DisiloxaneHCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 54223603HCID 54223603, compoundYield 88%

Procedure

To a solution of the silylether prepared in 1N (237 mg, 0.43 mmole) in tetrahydrofuran (5 ml) was added tetra-n-butylammonium fluoride trihydrate (205 mg, 0.65 mmole). The mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure. The residue was dissolved in methylene chloride, washed with water and dried over sodium sulfate. Filtration and concentration under reduced pressure afforded an oil. Flash chromatography on silicagel and elution with a 15:95 mixture of ethyl-acetate and benzene afforded the expected alcohol as an oil (119 mg, 88%). NMR (H1, CDCl3, 360 MHz) characteristic peaks: 2.32 (dm, JHF =21.6 Hz, 2), 2.72 (t, JHH =7 HZ, 2), 3.73 (m, 2), 5.09 (dt, JHF =21.6 Hz, JHH =8 Hz, 1), 5.39 (m, 4).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration under reduced pressure
  6. customafforded an oil
  7. washFlash chromatography on silicagel and elution
  8. additionwith a 15:95 mixture of ethyl-acetate and benzene

Sources & evidence

ORD record
ord-807c7e46ffd24875b4d6355dd7829650
Source dataset
uspto-grants-1992_09
Patent number
US05145861

Reaction notes

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