Tetrabutylammonium Fluoride → HCID 15649678, compound

HRID 466807Notes

Reaction equation

HRID 466807 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 8028TetrahydrofuranSolvent2×

Procedure

Dissolve (3R,4R)-4-methoxy-4-methyl-1-trimethylsilyl-1-octyn-3-ol (40 mg, 0.17 mmol) in tetrahydrofuran (1 mL) and place under an argon atmosphere. Add, by dropwise addition, tetra-n-butylammonium fluoride (1.4 mL of a 1M 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-6a36b9f3df3f4c918422362db2506d9c
Source dataset
uspto-grants-1992_10
Patent number
US05157167

Reaction notes

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