Diethyl (ethoxymethylene)malonate → Diethyl [1-ethoxy-2-(6-mesitylpyridin-2-yl)-3-oxohexyl]malonate

HRID 598111ノート

反応式

HRID 598111 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[C:13]1([CH3:33])[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](=[O:32])[CH2:29][CH2:30][CH3:31])[CH:24]=[CH:23][CH:22]=1.[CH3:34][CH2:35][O:36][CH:37]=[C:38]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[C:39]([O:41][CH2:42][CH3:43])=[O:40]>O1CCCC1>[CH2:35]([O:36][CH:37]([CH:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH:27]([C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([C:14]2[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=2[CH3:33])[N:26]=1)[C:28](=[O:32])[CH2:29][CH2:30][CH3:31])[CH3:34]

参加物

6

反応物 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7912DiisopropylamineHCID 672671441-(6-Mesitylpyridin-2-yl)pentan-2-oneHCID 178418339Butyllithium

生成物 1

HCID 67267834Diethyl [1-ethoxy-2-(6-mesitylpyridin-2-yl)-3-oxohexyl]malonate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Diisopropyl amine (0.16 mL, 1.13 mmol) was dissolved in tetrahydrofuran (2 mL). n-Butyllithium (2.5M, 0.45 mL, 1.13 mmol) was added at 0° C. and the reaction stirred for 0.5 h. The solution was cooled to −78° C. and 1-(6-mesityl-pyridin-2-yl)-pentan-2-one (0.29 g, 1.0 mmol) was added. After 0.5 h, ethyl ethoxymethylene malonate (0.21 mL, 1.0 mmol) was added and the reaction was warmed to room temperature. The solution was quenched with water, extracted with ethyl acetate, dried, and concentrated. Flash chromatography (10%-20% ethyl acetate/hexanes) gave the title compound as a mixture of two isomers.

後処理

  1. waitAfter 0.5 h
  2. temperaturethe reaction was warmed to room temperature
  3. customThe solution was quenched with water
  4. extractionextracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c85721d5e3364b6eaca24aefab935b67
出典データセット
uspto-grants-2011_03
特許番号
US07897607B2

反応ノート

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