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

HRID 1473121ノート

反応式

HRID 1473121 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-741357864cfd4a1ea927ac27110e0c56
出典データセット
uspto-grants-2015_04
特許番号
US09012461B2

反応ノート

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