Tetrabutylammonium Fluoride → 2-(5-Ethynyl-indol-1-yl)-ethanol

HRID 271724Notes

Reaction equation

HRID 271724 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C[Si]([C:23]#[C:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([CH2:34][CH2:35][OH:36])[CH:29]=[CH:28]2)(C)C>C1COCC1>[C:24]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([CH2:34][CH2:35][OH:36])[CH:29]=[CH:28]2)#[CH:23]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 673645732-(5-Trimethylsilanylethynyl-indol-1-yl)-ethanol

Product 1

HCID 859695012-(5-Ethynyl-indol-1-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an N2 atmosphere 29 g (91.8 mmol) TBAF are added to a solution of 21.5 g (83.5 mmol) 2-(5-trimethylsilanylethynyl-indol-1-yl)-ethanol in 500 mL THF and the reaction mixture is stirred for 1.5 h at RT. The mixture is evaporated down i.vac., the residue is taken up in 300 mL EtOAc, the organic phase is washed twice with in each case 200 mL water and once with 200 mL saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the desired product is obtained in the form of a brown oil.

Workup

  1. customThe mixture is evaporated down i.vac
  2. washthe organic phase is washed twice with in each case 200 mL water and once with 200 mL saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis obtained in the form of a brown oil

Sources & evidence

ORD record
ord-6f6fac28a2a74bc4b159ee0b6b7e0c66
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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