Water → Ethyl 2-(3-ethynylpyrazin-2-yl)acetate

HRID 1473121Notes

Reaction equation

HRID 1473121 reaction equation
C[Si]([C:5]#[C:6][C:7]1[C:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:9][CH:10]=[CH:11][N:12]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[C:6]([C:7]1[C:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:9][CH:10]=[CH:11][N:12]=1)#[CH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 68282873Ethyl 2-(3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetate

Product 1

HCID 86675726Ethyl 2-(3-ethynylpyrazin-2-yl)acetateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 2-(3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetate (I100) (0.386 g, 1.47 mmol) in THF (15 mL) was cooled to 0° C. and a 1.0 M solution of TBAF in THF (1.84 mL, 1.84 mmol) was added. The mixture was stirred for two minutes then poured into water (150 mL). The resulting mixture was extracted with diethyl ether (2×150 mL) and the combined ether phases washed with brine, dried (sodium sulphate) and evaporated to give the title compound (I101) (0.209 g, 75% yield) as a yellow-brown oil; 1H NMR (400 MHz, CDCl3) δ 8.50-8.47 (m, 2H), 4.21 (q, J=7.1 Hz, 2H), 4.08 (s, 2H), 3.49 (s, 1H), 1.26 (t, J=7.1 Hz, 3H). LCMS Method C: rt 4.88 min; m/z 191.1 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with diethyl ether (2×150 mL)
  2. washthe combined ether phases washed with brine
  3. dry with materialdried (sodium sulphate)
  4. customevaporated

Sources & evidence

ORD record
ord-741357864cfd4a1ea927ac27110e0c56
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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