Tetrabutylammonium Fluoride → 1-[2-(4-Ethynyl-phenoxy)-ethyl]-pyrrolidine

HRID 1916522Notes

Reaction equation

HRID 1916522 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:20]=[CH:19][C:10]([O:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:9][CH:8]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:6]([C:7]1[CH:20]=[CH:19][C:10]([O:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)=[CH:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 673634551-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

Product 1

HCID 859698151-[2-(4-Ethynyl-phenoxy)-ethyl]-pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere a solution of 12.8 g (44.5 mmol) 1-[2-(4-trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine in 200 mL THF is combined with 15.5 g (49.0 mmol) TBAF and stirred for 3 h at RT. The solvent is distilled off i.vac., the residue taken up in EtOAc, the organic phase is washed with saturated, aqueous NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the product is further reacted without any purification.

Workup

  1. distillationThe solvent is distilled off i.vac
  2. washthe organic phase is washed with saturated, aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis further reacted without any purification

Sources & evidence

ORD record
ord-42de2b1666ee4ba2acf6aae17429d693
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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