Tetrahydrofuran → HCID 54334725, compound

HRID 1885641Notes

Reaction equation

HRID 1885641 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: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])=[CH:21][CH2:29][CH2:28][CH2:27][CH2:26][OH:25]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 123318DisiloxaneHCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 54334725HCID 54334725, compoundYield 68%

Procedure

To a solution of the silylether (58 mg, 0.1 mmole) in tetrahydrofuran (2 ml) was added tetra-n-butylammonium fluoride trihydrate (50 mg, 0.15 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 2:8 mixture of ethyl acetate and hexane afforded the expected alcohol as an oil (21 mg, 68%).

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 2:8 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-2dba965dd7e04075b16bf51d9b315d34
Source dataset
uspto-grants-1992_09
Patent number
US05145861

Reaction notes

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