Tetrabutylammonium Fluoride → alpha-Ethynylbenzenemethanol

HRID 1654766Notes

Reaction equation

HRID 1654766 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]-benzenemethanol (1.87 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 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-9d447879e8bb4584bd034dbb3e4e51d4
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

Loading…