Tetrabutylammonium Fluoride → alpha-Ethynylbenzenemethanol

HRID 1588718

Reaction equation

HRID 1588718 reaction equation
C[Si]([C:5]#[C:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:6]([CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8])#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 27604161-Phenyl-3-(trimethylsilyl)-2-propyn-1-ol

Product 1

HCID 20155alpha-Ethynylbenzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Place a mixture of α-[(trimethylsilyl)ethynyl]-benzene-methanol (1.87 g, 9.13mmol) 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 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-3c830598d89149feb4735d7649e831d5
Source dataset
uspto-grants-1993_06
Patent number
US05223518

Linked notes

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