Hydrogen Peroxide → 4-nitro-2,3-dihydro-1H-inden-2-yl acetate

HRID 1434558

반응식

HRID 1434558 반응식
CC(=C(C)C)C.B.C1COCC1.[N+:13]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:24]=1[CH2:23][CH:22]=[CH:21]2)([O-:15])=[O:14].[OH-].[Na+].OO.[C:29]([O:32]C(=O)C)(=[O:31])[CH3:30]>C1COCC1.C1(C)C=CC=CC=1.N1C=CC=CC=1.O>[C:29]([O:32][CH:22]1[CH2:23][C:24]2[C:20](=[CH:19][CH:18]=[CH:17][C:16]=2[N+:13]([O-:15])=[O:14])[CH2:21]1)(=[O:31])[CH3:30]

참가 물질

11

반응물 6

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 112502,3-Dimethyl-2-buteneHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 132395877-nitro-1H-indene

생성물 1

HCID 132395834-nitro-2,3-dihydro-1H-inden-2-yl acetate수율 25.8%

시약·촉매·용매 4

HCID 962Water용매2회HCID 1049Pyridine용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 2,3-dimethyl-2-butene (21.5 mg, 0.31 mmol) in THF (2 ml) at 0° C. was added borane-THF (0.307 ml, 0.31 mmol) dropwise. After stirred for 1 hour at 0° C., 7-nitro-1H-indene (45.0 mg, 0.28 mmol) in THF (5 ml) was added dropwise, and the mixture was stirred for 2 hours at ambient temperature. The mixture was cooled to 0° C., and water (0.15 ml), 4N aqueous sodium hydroxide (0.45 ml), and 30% H2O2 (0.45 ml) were added. The mixture was then warmed to room temperature and poured into water, extracted with ethyl acetate and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. To the obtained mixture in toluene (1 ml) was added acetic anhydride (40.8 mg, 0.40 mmol) and pyridine (0.4 ml), and then stirred for 16 hours at room temperature. The mixture was concentrated under reduced pressure, and the obtained residue was purified by preparatory TLC (hexane:ethylacetate 2:1) to obtain 4-nitro-2,3-dihydro-1H-inden-2-yl acetate (16.0 mg).

후처리

  1. stirringthe mixture was stirred for 2 hours at ambient temperature
  2. temperatureThe mixture was cooled to 0° C.
  3. temperatureThe mixture was then warmed to room temperature
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. stirringstirred for 16 hours at room temperature
  10. concentrationThe mixture was concentrated under reduced pressure
  11. customthe obtained residue was purified by preparatory TLC (hexane:ethylacetate 2:1)

출처 및 근거

ORD 기록
ord-554be209bdd74171846f39b6ffcba9eb
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615557B2

연결된 노트

불러오는 중…