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Diethyl (ethoxymethylene)malonate → HCID 86613888、化合物

HRID 598106
ノート
印刷プレビュー

反応式

HRID 598106 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[C:13]1([CH3:30])[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:14]=1[C:21]1[N:26]=[C:25]([CH2:27][C:28]#[N:29])[CH:24]=[CH:23][CH:22]=1.C([O:33][CH:34]=[C:35]([C:41](OCC)=O)[C:36]([O:38][CH2:39][CH3:40])=[O:37])C>O1CCCC1.C(O)(=O)C>[C:28]([C:27]1[CH:41]=[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:34](=[O:33])[N:26]2[C:25]=1[CH:24]=[CH:23][CH:22]=[C:21]2[C:14]1[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[CH3:30])#[N:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7912DiisopropylamineHCID 672670006-(2,4,6-Trimethylphenyl)-2-pyridineacetonitrileHCID 178418339Butyllithium

生成物 1

HCID 86613888HCID 86613888、化合物収率 84.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

Diisopropylamine (1.6 mL, 11.6 mmol) in tetrahydrofuran (15 mL) was charged with n-butyllithium (2.5M, 4.6 mL, 11.6 mmol) at 0° C. The reaction stirred for 0.5 h. The solution was cooled to −20° C. and (6-mesitylpyridin-2-yl)acetonitrile (2.49 g, 10.5 mmol) was added drop wise (as a solution in 5 mL tetrahydrofuran). After 0.5 h, the solution was cooled to −78° C. and diethyl ethoxymethylenemalonate (2.1 mL, 10.5 mmol) was added. The reaction stirred for 0.5 h and was then cooled to room temperature. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to give an orange residue. The material was dissolved in acetic acid (20 mL) and heated at 100° C. for 4 h. The solution was cooled and poured into an Erlenmeyer flask and washed with water. The solution was neutralized with saturated sodium bicarbonate. The solution was extracted with ethyl acetate (3 times), dried, and concentrated. Flash chromatography (25% ethyl acetate/hexanes) gave 3.19 g (84% yield) of the title compound as a yellow solid.

後処理

  1. waitAfter 0.5 h
  2. temperaturethe solution was cooled to −78° C.
  3. stirringThe reaction stirred for 0.5 h
  4. temperaturewas then cooled to room temperature
  5. customThe reaction was quenched with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an orange residue
  11. temperatureheated at 100° C. for 4 h
  12. temperatureThe solution was cooled
  13. additionpoured into an Erlenmeyer flask
  14. washwashed with water
  15. extractionThe solution was extracted with ethyl acetate (3 times)
  16. customdried
  17. concentrationconcentrated

出典と根拠

ORDレコード
ord-80cd84f48efa4ab0a310ed7675d60ed9
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07897607B2

反応ノート

読み込み中…

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