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

HRID 598111노트

반응식

HRID 598111 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c85721d5e3364b6eaca24aefab935b67
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

반응 노트

불러오는 중…