Sodium Hydroxide → 4-(Benzyloxy)-2-[(heptylsulfinyl)methyl]-3-methylquinoline

HRID 384442

Reaktionsgleichung

Reaktionsgleichung von HRID 384442
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:10]=1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:37])C=1.[OH-].[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][S:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:37])[C:10]=1[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 595272964-(Benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline

Produkt 1

HCID 595273144-(Benzyloxy)-2-[(heptylsulfinyl)methyl]-3-methylquinolineAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline (106 mg) in dichloromethane (5 mL) was added m-chloroperbenzoic acid (75%, 68 mg) at −30° C., followed by stirring for 5 hours while warming to room temperature. A 0.2M aqueous sodium hydroxide solution (20 mL) was added to the reaction mixture, followed by extraction with chloroform (50 mL). The organic layer was washed sequentially with water and saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to obtain 4-(benzyloxy)-2-[(heptylsulfinyl)methyl]-3-methylquinoline (75 mg).

Aufarbeitung

  1. extractionfollowed by extraction with chloroform (50 mL)
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-d58d66f255d94c5cbadca1ba63e3abc4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367702B2

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