Methane, dichloromethoxy- → 2-Methoxy-5-(5-methyl-7-nitroindan-4-yloxy)benzaldehyde

HRID 1766646노트

반응식

HRID 1766646 반응식
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[C:13]3[C:9]=2[CH2:10][CH2:11][CH2:12]3)=[CH:5][CH:4]=1.[CH3:23][O:24]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[C:13]3[C:9]=2[CH2:10][CH2:11][CH2:12]3)=[CH:5][C:4]=1[CH:23]=[O:24]

참가 물질

5

반응물 2

HCID 21004Methane, dichloromethoxy-HCID 230311142,3-Dihydro-4-(4-methoxyphenoxy)-5-methyl-7-nitro-1H-indene

생성물 1

HCID 230312052-Methoxy-5-(5-methyl-7-nitroindan-4-yloxy)benzaldehyde

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

실험 절차

4-(4-methoxyphenoxy)-5-methyl-7-nitroindane (5.0 g) and dichloromethyl methyl ether (3.02 mL) were dissolved in dichloromethane (50 mL). To the solution was added dropwise titanium tetrachloride (3.67 mL) under ice-cooling with stirring. The reaction mixture was stirred at room temperature under an argon atmosphere for 20 hours. After adding ice water (300 mL), the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was triturated with hexane (50 mL) and diethyl ether (5 mL), and the insoluble material was collected by filtration and washed with hexane to give the title compound (4.37 g).

후처리

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature under an argon atmosphere for 20 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was triturated with hexane (50 mL) and diethyl ether (5 mL)
  8. filtrationthe insoluble material was collected by filtration
  9. washwashed with hexane

출처 및 근거

ORD 기록
ord-e1ac0c6ed2244fd2afa6481a2c629b3e
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230031B2

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