Tert-Butyl nitrite → 1-(2-Acetoxymethyl-2-propenyl)-3,5-dinitrobenzene

HRID 1595007노트

반응식

HRID 1595007 반응식
C(ON=O)(C)(C)C.[C:8]([O:11][CH2:12][C:13]([CH2:15]Br)=[CH2:14])(=[O:10])[CH3:9].[N+:17]([C:20]1[CH:21]=[C:22]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)N)([O-:19])=[O:18]>CC#N>[C:8]([O:11][CH2:12][C:13](=[CH2:14])[CH2:15][C:22]1[CH:21]=[C:20]([N+:17]([O-:19])=[O:18])[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=1)(=[O:10])[CH3:9]

참가 물질

5

반응물 3

HCID 10906Tert-Butyl nitriteHCID 120683,5-DinitroanilineHCID 14664197HCID 14664197, 화합물

생성물 1

HCID 98821461-(2-Acetoxymethyl-2-propenyl)-3,5-dinitrobenzene수율 74.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of t-butylnitrite (0.47 ml, 4.0 mmol) and 2-acetoxymethyl-3-bromopropene (1.93 g, 10.0 mmol) in 1 ml CH3CN, 3,5-dinitroaniline (0.37 g, 2.0 mmol) was added, while maintaining the temperature between 18 and 24° C. The mixture was stirred for 1 h at room temperature. The volatile material in the solution was removed at reduced pressure. Flash chromatography (heptane/ethylacetate) gave 0.42 g 1-(2-acetoxymethyl-2-propenyl)-3,5-dinitrobenzene. 1H-NMR (CDCl3, 300 MHz) δ ppm: 8.94 (t, J=2.1 Hz, 1H), 8.42 (d, J=2.1 Hz, 2H), 5.33 (s, 1H), 5.05 (s, 1H), 4.52 (s, 2H), 3.64 (s, 2H), 2.08 (s, 3H). 13C-NMR (CDCl3, 75.43 MHz) δ ppm: 170.4, 148.5, 143.1, 140.7, 129.1, 117.5, 117.2, 65.9, 39.3, 20.7.

후처리

  1. temperaturewhile maintaining the temperature between 18 and 24° C
  2. customThe volatile material in the solution was removed at reduced pressure

출처 및 근거

ORD 기록
ord-356844faf6af4ae39656ec73632d4574
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06284894B1

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