Tetrabutylammonium Fluoride → 3-Methyl-1-nonyn-3-ol

HRID 466810Notes

Reaction equation

HRID 466810 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]([CH3:13])([OH:12])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:13][C:5]([OH:12])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:4]#[CH:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15649677HCID 15649677, compound

Product 1

HCID 2251503-Methyl-1-nonyn-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 1-trimethylsilyl-3-methyl-1-nonyn-3-ol (1.94 g, 9.13 mmol) in tetrahydrofuran (11 mL) and place under an argon atmosphere. Add, by dropwise addition, tetra-n-butylammonium fluoride (11 mL of a 1M solution in tetrahydrofuran, 11 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, dry (MgSO4), filter and evaporate the solvent in vacuo to give the title compound.

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. filtrationfilter
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-830f8230334a4c39a1a8822d9df2d317
Source dataset
uspto-grants-1992_10
Patent number
US05157167

Reaction notes

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