Tetrabutylammonium Fluoride → HCID 11095065, compound

HRID 466806Notes

Reaction equation

HRID 466806 reaction equation
[CH3:1][O:2][C@:3]([CH3:16])([CH2:12][CH2:13][CH2:14][CH3:15])[C@@H:4]([OH:11])[C:5]#[C:6][Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C@:3]([CH3:16])([CH2:12][CH2:13][CH2:14][CH3:15])[C@@H:4]([OH:11])[C:5]#[CH:6]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 11053841HCID 11053841, compound

Product 1

HCID 11095065HCID 11095065, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve (3S,4R)-4-methoxy-4-methyl-1-trimethylsilyl-1-octyn-3-ol (90 mg, 0.37 mmol) in tetrahydrofuran (2 mL) and place under an argon atmosphere. Add, by dropwise addition, tetra-n-butylammonium fluoride (3.7 mL) of a 1M solution in tetrahydrofuran, 3.7 mmol). Stir for 1 hour at room temperature and partition between methylene chloride and water. Separate the organic phase, wash with saturated aqueous sodium chloride and dry (MgSO4). Evaporate the solvent in vacuo and purify by silica gel chromatography (19:1 hexane/ethyl acetate) to give the title compound as a clear thick oil (55 mg, 87%).

Workup

  1. custompartition between methylene chloride and water
  2. customSeparate the organic phase
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by silica gel chromatography (19:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7879d9225a3645bca1f7d1c4d7c9d522
Source dataset
uspto-grants-1992_10
Patent number
US05157167

Reaction notes

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