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

HRID 1916756Notes

Reaction equation

HRID 1916756 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

A reaction mixture of 1.22 g (4.24 mmol) 1-[2-(4-trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine, 1.47 g (4.67 mmol) TBAF and 25 mL THF is stirred for 3 h at RT. Then the reaction mixture is evaporated down and the residue is combined with 20 mL saturated NaCl solution and 50 mL EtOAc. The organic phase is dried over Na2SO4. The purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 90:10:1).

Workup

  1. customThen the reaction mixture is evaporated down
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customThe purification

Sources & evidence

ORD record
ord-ce9ccea801b746c0aca766df5c6f330e
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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