Tetrabutylammonium Fluoride → HCID 2749588, compound

HRID 1654758Notes

Reaction equation

HRID 1654758 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]#[C:12][Si](C)(C)C)[OH:10])=[CH:5][CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]#[CH:12])[OH:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10911866HCID 10911866, compound

Product 1

HCID 2749588HCID 2749588, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Place a mixture of 4-dimethylamino-α-[(trimethylsilyl)ethynyl]-benzenemethanol (2.26 g, 9.13 mmol) and tetrahydrofuran (11 mL) under 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 ethyl ether and water. Separate the organic phase, wash with saturated aqueous sodium chloride, dry (MgSO4), filter, and concentrate in vacuo to yield 1.37 g, (85.6%) of the title compound.

Workup

  1. custompartition between ethyl ether and water
  2. customSeparate the organic phase
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-5853741e09db4c14ad30d36e25c703b0
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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