Tetrabutylammonium Fluoride → 2-(2-Ethynylphenyl)propanamide

HRID 592357Notes

Reaction equation

HRID 592357 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C[Si]([C:23]#[C:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]([CH3:35])[C:32]([NH2:34])=[O:33])(C)C>C1COCC1.C([O-])(O)=O.[Na+]>[C:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]([CH3:35])[C:32]([NH2:34])=[O:33])#[CH:23]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867122802-(2-((Trimethylsilyl)ethynyl)phenyl)propanamide

Product 1

HCID 867122792-(2-Ethynylphenyl)propanamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A 1.0 M solution of TBAF in THF (45.6 mL, 45.6 mmol) was added to a solution of 2-(2-((trimethylsilyl)ethynyl)phenyl)propanamide I15 (9.33 g, 38.0 mmol) in THF (200 mL) and the mixture was stirred for 10 minutes. The reaction mixture was diluted with sat. aq. NaHCO3 (200 mL), and the aqueous layer was extracted with DCM (3×150 mL). The combined organics were adsorbed onto silica and purified by silica gel column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 0-80% EtOAc in petroleum benzine 40-60° C.) to yield the title compound K7 as a tan solid (5.11 g, 76%). LCMS-D: rt 3.03 min; m/z 174 [M+H]+.

Workup

  1. extractionthe aqueous layer was extracted with DCM (3×150 mL)
  2. custompurified by silica gel column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 0-80% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-f73f952dec364400a637c6ece9b71df1
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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