Tetrabutylammonium Fluoride → HCID 15649678, compound

HRID 1195410Notes

Reaction equation

HRID 1195410 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 15649676HCID 15649676, compound

Product 1

HCID 15649678HCID 15649678, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (3R,4R)-4-methoxy-4-methyl-l-trimethylsilyl-l-octyn-3-ol (40mg, 0.17 mmol) in tetrah place under an argon atmosphere. Add, by dropwise addition, tetra-n-butylammonium fluoride (1.4 mL of a lM solution in tetrahydrofuran, 1.4 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 to give the title compound as a thick clear oil (21 mg, 75%).

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

Sources & evidence

ORD record
ord-7f83f6b5005d40e0b009b908437434e9
Source dataset
uspto-grants-1992_05
Patent number
US05110966

Reaction notes

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