Water → 3-Ethynylbenzamide

HRID 1473166Notes

Reaction equation

HRID 1473166 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([NH2:12])=[O:11])(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[C:6]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([NH2:12])=[O:11])#[CH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 682830043-((Trimethylsilyl)ethynyl)benzamide

Product 1

HCID 120650003-EthynylbenzamideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-((Trimethylsilyl)ethynyl)benzamide (I143) (0.565 g, 2.60 mmol) was dissolved in THF (33 mL), and 1 M TBAF in THF (3.25 mL, 3.25 mmol) was added. After two hours the reaction was poured into water (200 mL) and the resulting solution was extracted with diethyl ether (3×200 mL). The combined ether phases were washed with brine (200 mL), dried over sodium sulfate then evaporated to give the title compound (I144) (0.357 g, 95% yield) as a tan solid; 1H NMR (400 MHz, CDCl3) δ 7.92 (t, J=1.5 Hz, 1H), 7.83-7.79 (m, 1H), 7.64 (dt, J=7.7, 1.4 Hz, 1H), 7.42 (td, J=7.8, 0.5 Hz, 1H), 6.07 (br s, 1H), 5.77 (br s, 1H), 3.13 (s, 1H). LCMS Method C: rt 4.74 min, m/z 146.2 [M+H]+.

Workup

  1. extractionthe resulting solution was extracted with diethyl ether (3×200 mL)
  2. washThe combined ether phases were washed with brine (200 mL)
  3. dry with materialdried over sodium sulfate
  4. customthen evaporated

Sources & evidence

ORD record
ord-b0a9a2cd3119440983dc6e68773e0b98
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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