Tetrabutylammonium Fluoride → N-(5-Ethynyl-2-methylphenyl)-2,2,2-trifluoroacetamide

HRID 1157630Notes

Reaction equation

HRID 1157630 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si](C)(C)C)[CH:9]=[CH:8][C:7]=1[CH3:18])=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[C:12]([C:10]1[CH:9]=[CH:8][C:7]([CH3:18])=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:19])([F:1])[F:20])[CH:11]=1)#[CH:13]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 595114182,2,2-Trifluoro-N-{2-methyl-5-[(trimethylsilyl)ethynyl]phenyl}acetamide

Product 1

HCID 57737207N-(5-Ethynyl-2-methylphenyl)-2,2,2-trifluoroacetamideYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,2,2-trifluoro-N-{2-methyl-5-[(trimethylsilyl)ethynyl]phenyl}-acetamide (10.9 g, 36 mmol) in THF (350 mL) cooled to 0° C. was added a 1M solution of tetrabutylammonium fluoride in THF (40 mmol, 40 mL). The reaction was diluted with water and extracted two times with EtOAc. The combined organic extractions were washed with water, dried over MgSO4 and concentrated onto silica gel. The crude material was purified by column chromatography to give the desired product (6.4 g, 78%). 1H NMR (400 MHz, d6-DMSO) δ 11.00 (s, 1H), 7.36-7.30 (m, 3H), 4.19 (s, 1H), 2.17 (s, 3H) ppm.

Workup

  1. extractionextracted two times with EtOAc
  2. extractionThe combined organic extractions
  3. washwere washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated onto silica gel
  6. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-8bba41d2f4c44b1a89f90b6f72495a88
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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