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

HRID 1473121노트

반응식

HRID 1473121 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-741357864cfd4a1ea927ac27110e0c56
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012461B2

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