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

HRID 1473121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473121
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-741357864cfd4a1ea927ac27110e0c56
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012461B2

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