Tetrabutylammonium Fluoride → N-(4-Ethynylphenethyl)acetamide

HRID 76166Notes

Reaction equation

HRID 76166 reaction equation
[Si]([C:8]#[C:9][C:10]1[CH:21]=[CH:20][C:13]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)Cl>[C:9]([C:10]1[CH:21]=[CH:20][C:13]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1)#[CH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66611489N-(4-((tert-butyldimethylsilyl)ethynyl)phenethyl)acetamide

Product 1

HCID 87073685N-(4-Ethynylphenethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2.20 g (7.30 mmol) N-(4-((tert-butyldimethylsilyl)ethynyl)phenethyl)acetamide (I56.1) in 30 mL DCM are added 2.24 g (8.03 mmol) TBAF*H2O and the mixture is stirred at r.t. over night. The mixture is washed with water (2×). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH 10/0→20/1).

Workup

  1. washThe mixture is washed with water (2×)
  2. dry with materialThe organic layer is dried with Na2SO4
  3. customthe solvent is removed in vacuo
  4. customThe crude product is purified by column chromatography (silica gel, DCM/MeOH 10/0→20/1)

Sources & evidence

ORD record
ord-d4911b273d7547888a32647d4b9b6644
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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