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

HRID 1485235ノート

反応式

HRID 1485235 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-020a86ab029e47818db10b8f8f9ff814
出典データセット
uspto-grants-2016_08
特許番号
US09421205B2

反応ノート

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