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Chloroform → 5-Chloromethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1678336
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Reaktionsgleichung

Reaktionsgleichung von HRID 1678336
O[CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH3:24])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:27])=[CH:6][C:7]([CH3:26])([CH3:25])[NH:8]2.C(N(CC)CC)C.CS([Cl:39])(=O)=O.C(Cl)(Cl)Cl>C(Cl)Cl.O>[Cl:39][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH3:24])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:27])=[CH:6][C:7]([CH3:26])([CH3:25])[NH:8]2
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Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 579905855-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Produkt 1

HCID 579906385-Chloromethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinolineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 1, 1.02 g, mmol) was dissolved in anhydrous methylene dichloride (10 mL), and then triethylamine (0.490 mL, 3.52 mmol) and methanesulfonyl chloride (231 L, mmol) were added successively. The reaction mixture was stirred at room temperature for 5 hours. Chloroform (50 mL) and water (50 mL) were added to the reaction mixture and separated. The organic layer was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (515 mg) as an orange amorphous product. (Yield 49%)

Aufarbeitung

  1. customseparated
  2. washThe organic layer was washed with saturated brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9ab92a502fde4202b052b13f49c0a5a4
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08008498B2

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