Potassium Carbonate → t-Butyl ethyl (2,4-dinitronaphthalen-1-yl)malonate

HRID 431729노트

반응식

HRID 431729 반응식
C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N+:18]([O-:20])=[O:19])=[CH:10][C:9]=1[N+:21]([O-:23])=[O:22].[C:24]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C1COCC1>[N+:21]([C:9]1[CH:10]=[C:11]([N+:18]([O-:20])=[O:19])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:24]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])([O-:23])=[O:22]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 169871-Chloro-2,4-dinitronaphthaleneHCID 96345tert-Butyl ethyl malonate

생성물 1

HCID 11452450t-Butyl ethyl (2,4-dinitronaphthalen-1-yl)malonate수율 78.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

K2CO3 (4.04 g, 29.22 mmol) was added to a solution of 1-chloro-2,4-dinitronaphthalene (6.04 g, 23.91 mmol) and t-butyl ethyl malonate (5.0 g, 26.50 mmol) in THF (50 mL), and the mixture was heated reflux overnight. The mixture was cooled and filtered, then the filtrate was concentrated under reduced pressure. Flash chromatography (20-50% AcOEt-Petroleum ether gradient elution) afforded t-butyl ethyl (2,4-dinitronaphthalen-1-yl)malonate (7.6 g, 54%) as a pale red solid. M.p. 86-88° C.; 1H NMR (CDCl3, 500 MHz) δ 8.65 (s, 1H), 8.55 (dd, 0.5, 8.5, 1H), 8.36 (dd, 0.5, 9.0, 1H), 7.89 (dt, 1.0, 8.0, 1H), 7.81 (dt, 1.5, 9.0, 1H), 5.64 (s, 1H), 4.26 (q, 7.0, 2H), 1.44 (s, 9H), 1.24 (t, 7.0, 3H); IR (neat) 2980, 1745, 1537, 1368, 1346, 1306, 1253, 1147, 1027, 850, 832, 801, 774, 761 cm−1. FABMS (NBA) m/z 405 (M+H+, 5).

후처리

  1. temperaturethe mixture was heated
  2. temperaturereflux overnight
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washFlash chromatography (20-50% AcOEt-Petroleum ether gradient elution)

출처 및 근거

ORD 기록
ord-c72f337d4fe748be88c9b2631c84dedf
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660742B2

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