Tetrabutylammonium Fluoride → HCID 11095065, compound

HRID 1195409Notes

Reaction equation

HRID 1195409 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 8028TetrahydrofuranSolvent

Procedure

Dissolve (3S,4R)-4-methoxy-4-methyl-l-trimethylsilyl-l-octyn-3-ol (90 mg, 0.37 mmol) in tetrahydrofu 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-9f43079c2251424ba5d20a93285558d5
Source dataset
uspto-grants-1992_05
Patent number
US05110966

Reaction notes

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