Cyclohexanol, 1-((trimethylsilyl)ethynyl)- → 1-Ethynylcyclohexanol

HRID 466808Notes

Reaction equation

HRID 466808 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:4]([C:5]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)#[CH:3]

Participants

4

Reactant 2

HCID 205445Cyclohexanol, 1-((trimethylsilyl)ethynyl)-HCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 65251-Ethynylcyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 1-(2-trimethylsilyl-1-ethynyl)cyclohexanol (1.79 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-9407aa3917b1401fb09b205273d463da
Source dataset
uspto-grants-1992_10
Patent number
US05157167

Reaction notes

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