Ethanol → Diethyl-2-(1-pyrenylmethyl)-2-acetamidomalonate

HRID 1070366노트

반응식

HRID 1070366 반응식
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[H-].[Na+].C(O)C.Br[CH2:22][C:23]1[C:36]2[C:37]3=[C:38]4[C:33](=[CH:34][CH:35]=2)[CH:32]=[CH:31][CH:30]=[C:29]4[CH:28]=[CH:27][C:26]3=[CH:25][CH:24]=1>C1COCC1>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:22][C:23]1[C:36]2[C:37]3=[C:38]4[C:33](=[CH:34][CH:35]=2)[CH:32]=[CH:31][CH:30]=[C:29]4[CH:28]=[CH:27][C:26]3=[CH:25][CH:24]=1)([NH:4][C:1](=[O:3])[CH3:2])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:10]

참가 물질

6

반응물 4

HCID 702EthanolHCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 12740433-(Bromomethyl)pyrene

생성물 1

HCID 22395542Diethyl-2-(1-pyrenylmethyl)-2-acetamidomalonate수율 83.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 9.78 g (45.04 mmol) sample of diethyl acetamidomalonate, and 1.08 g sodium hydride (45.04 mmol) were suspended in 100 mL of anhydrous THF, under nitrogen, and at 0°C. After stirring for 5 min., 2.5 mL of anhydrous ethanol were added slowly, and the solution returned to room temperature. A solution of 1-(bromomethyl)pyrene (12.03 g, 40.9 mmol, dissolved in 100 mL dry THF) was slowly added to the reaction mixture, and the solution brought to reflux for 18 h. The bulk of the THF was removed under reduced pressure, and the remaining yellow slurry was dissolved in 400 mL 1:1 CH2Cl2:H2O. The organic fraction was washed 3× with 100 mL H2O, and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to produce Diethyl-2-(1-pyrenylmethyl)-2-acetamidomalonate (14.70 g, 83.1%) as a light yellow powder. TLC (SiO2, 1:1 Hexane:EtOAc) Rƒ=0.57. Mp=135-140° C. 1H NMR (CDCl3), δ1.37 (t, 6H), 1.95 (s, 3H), 3.76 (s, 2H), 4.30 (q, 6H), 6.42 (s, NH), 8.00-825 (m, 9H from pyrene).

후처리

  1. customat 0°C
  2. customreturned to room temperature
  3. temperatureto reflux for 18 h
  4. customThe bulk of the THF was removed under reduced pressure
  5. dissolutionthe remaining yellow slurry was dissolved in 400 mL 1:1 CH2Cl2
  6. washThe organic fraction was washed 3× with 100 mL H2O
  7. dry with materialdried over anhydrous Na2SO4
  8. customSolvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-473c372186044f259f42cd8a49ea3297
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06902720B2

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